Where do you decide to city when you work remotely and have too many options? Analysis paralysis!

Welcome & Getting Started
1

Hi everyone! My husband and I are newer to TrustedHousesitters and are trying to figure out what works best for us when choosing sits around the U.S.

We both enjoy staying in houses and experiencing different areas, but we’re not really travelers who plan trips around tourist attractions, festivals, or specific events. My husband also works remotely, so the house and surrounding area itself are a big part of what makes a sit appealing to us.

I’d love to hear how more experienced sitters handle these three things:

1. How do you decide where you actually want to house sit?

If you’re not traveling for a particular event or attraction, how do you choose a destination?

Do you mainly look for:

  • A house you really like?

  • A particular type of pet?

  • A quiet or interesting area?

  • Nature, restaurants, walkability, weather, etc.?

  • Or do you pick the destination first and then look for a sit there?

We’re currently focusing on sits within the U.S., and I’m especially curious how others narrow down all the possibilities.

2. How do you handle transportation when the sit is far from home?

For example, if we’re coming from Florida and doing a sit in a smaller town in upstate New York, how do most sitters handle getting around?

Do you usually:

  • Fly in and rent a car?

  • Use Uber/Lyft or other rideshare services?

  • Use public transportation?

  • Occasionally get picked up by the homeowner?

  • Choose sits specifically based on whether a car is provided or available?

I’d especially love to hear from people who do sits in smaller towns or more rural areas where rideshare may not be practical.

3. What is considered normal or appropriate when having groceries delivered to a house sit?

We use services like Instacart, Shipt, and Target delivery at home and would much rather have groceries delivered than spend part of our trip grocery shopping.

Is it generally considered perfectly fine to have grocery deliveries sent to the house where you’re sitting?

Do you:

  • Have groceries delivered after you arrive?

  • Schedule a delivery for shortly after check-in?

  • Ask the homeowner first?

  • Use the homeowner’s address normally during the sit?

I’m curious what other sitters usually do and whether there are any etiquette issues we should know about.

Thanks! I’d love to hear how experienced sitters approach these things, especially other couples who work remotely or prefer quieter, more residential stays.

2

Hi @GirlOnFire

Welcome to the Forum!

I’ll let our members offer their unique perspectives, but to help you get started, here’s a few useful forum discussions that may be useful;

  1. Looking for help securing my first TrustedHousesitters sit
  2. Top 3 do’s and don’t for new TrustedHousesitter members
  3. Follow these steps to add your THS profile to your forum account - Forum members can then offer advice and recommendations which may help you stand out when you apply

Happy Housesitting!

3

We don’t travel for tourism, we travel to stay within a couple of hours of two sets of our family, in 2 different countries. We love staying in the local surroundings. We’re not manic city life people (our home is in a city - but it’s a bite-size tiny one), we love peace and quiet and a more friendly community vibe.

  1. It’s none of those you named for us. When we sit overseas we have a region/area in mind (so say 1-2hour travelling time), and our number 1 priority: “Is the nearest food shop less than a 20 min walk?” and are there off road walks within a few minutes of their home (regardless of whether it’s dogs or cats). If it doesn’t fit that, it’s ruled out for us.

  2. Can we get to their doorstep by plane, train, bus, taxi, or carshare. We rarely ask for a lift, it has happened, but it’s rare. We haven’t had the use of an owners car as yet, because we simply haven’t needed it, because we embrace whatever is local, we love it that way.

  3. Because we return to sit at some places, the owners fully ‘get’ our lifestyle and know occasionally we need to order ‘stuff’ to be delivered, whether it’s food, or any other type of supplies, so we don’t usually ask with those ones now. But if we were sitting for someone new, I’d word it in a way that they can’t say no, a sort-of expectant way “I am thinking of getting some things delivered from ?food shop/amazon?, I hope that’s okay with you… blablabla”… no one has ever said no.

It’s only ever been food or amazon deliveries with us, the owners know we have to eat, and the owners know amazon will have our official address account-wise, we’re not using their address. So they’re quite relaxed about it.

4

I think you are going to get a wide spectrum of responses to your post as everyone has different motivations for sitting. Some it’s about accommodation, some it’s about spending quality time with pets and for some, like us it’s all about travel.

We have a bucket list and first and foremost the sit has to be in an area on that list. From there many factors come into play but we have the luxury of time and transport options (flying, driving). Your lifestyle sounds quite different to ours but in time you will work out what works for you, what doesn’t work for you etc etc. Good luck and enjoy the experience.

5
  1. My approach with THS used to be: Location > consider sits available > if no appealing sit, then go on my own dime. And I used to telecommute from all sits.

Now on indefinite sabbatical, maybe retiring early, so I’m traveling more at my own expense, because I don’t need to telecommute, so I can sightsee more. I do sit some via my own network, but not nearly as much as when I used THS for telecommuting.

  1. For transportation, all of the above, depending on location and what I want to do.

  2. Grocery and meal delivery all the time. On some sits (and at some hotels), I’ve also had gifts delivered to take home. Saved me schlepping a lot. Though I love looking in person at supermarkets and drug stores abroad, I often still have stuff delivered. For sits, I wait till after I’ve arrived, so I can see what fridge and freezer space look like.

6

We would typically rent a car, especially if we plan to do some sightseeing in the area. A car offers the most flexibility, especially in rural areas and even suburbs of large cities. Pets are typically not allowed in rented vehicles, so if the owner expects you to take the dog to local dog parks, etc, this poses a problem which needs to be solved. Perhaps you can walk the dog in the neighborhood and skip the dog park. Perhaps the owner will let you use their car.

7

If you’re from the US and sitting in the US full time and one needs WiFi for their work, why not buy a campervan. Easier to have your own vehicle and you can park it in beautiful campsites between sits. That’s what I would do if doing this full time in my own country. Instead of packing and unpacking every two weeks, getting accommodations for in between sits, having to fly somewhere, having food you need to throw out as you didn’t use everything. Once you do a few sit you will know what you are looking for and target that. I would go from state to state and do one house country sit and one city sit in same area.

8

Yup, having an RV can work. Something to consider, size wise: In the U.S., some communities and jurisdictions have cracked down on parking RVs, especially overnight. And of course, size can make driving and parking harder in cities. Plus, many garages don’t have enough height clearance.

For online access, many RV’ers use Starlink, but you need to have clear access to satellites (like not be under trees). It doesn’t lock you into a subscription, which is nice, if you want to use it for spurts only.

Some folks sleep/camp in regular passenger cars, vans or such, because they can do it stealthily in more places, like in cities. Some make content about such, under the term “stealth camping.”

9

Hello and welcome to the world of housesitting.

My husband and I are full-time sitters from New Jersey. We have been doing this for 12 years now.

The first six years we sat in the US, we had a home base at my mom’s house in NJ and we did not have a car. So we would come back there for extended periods to visit with friends and family. But we did break things up with housesits. During that time almost all our US sits were in NYC since it was not far and you did not need a car to get there or get around.

My mom passed in May 2020 and after that we had a car. Once we sold her home a couple of months later, we started doing sits again. So our experience in regards to transportation seems different than yours as it does not sound like you have a car, or perhaps you do, but would not use it to travel to sits.

Obviously with a car, we can go anywhere and we don’t need to give thought to things like public transport,etc… So can’t be too helpful there.

We were lucky that even in the height of Covid, there were still people traveling. Since then we have spent more time in the US than we had prior, though we have still done plenty of sits abroad during these years. Our last stint abroad was 10 months from late 2024 to Sept 2025.

Until this last year or so, we mainly stuck to the East Coast for sits because we would fly back to NJ from abroad, pick up our car and try to spend some time with friends and family. During this time we did lots of sits in NY state and New England. We also have family in North Carolina so did numerous sits there and South Carolina as well as states along the way.

We drove out to the West Coast last Christmas for a sit in Las Vegas–stopping for sits in Tennessee and Arizona along the way-- and have been in California since January.

We usually base our travels on what sits pop up, though we may also set specific intentions to go specific places and keep an eye out for sits there in particular; but we are also flexible since largely basing our travels on what sits we see can easily alter our tentative plans.

Sometimes what we intend to do, and what we actually do end up quite different. When I first got to California, I would not have expected we would have stayed here for so long. We have sits booked through the end of January–with one gap we have to fill still–and have no plans to leave any time soon.

While we enjoy visiting a place that may have some sort of touristic appeal, as full-time sitters we stay in plenty of ‘regular’ places. We like more spacious accommodations when possible and would rather stay in a higher end suburban home than a small apartment in a huge city–the latter can be nice but generally we don’t do a lot of sits in super-urba locations . We particularly enjoy rural areas with scenic views. Being in California we have done a lot of sits in walking distance to the beach and we enjoy them a lot.

As full-time sitters especially, the overarching consideration for any sit I book is what will my day to day experience be like? If that doesn’t gel with my preferences, I know the location, the house, or anything else about the sit , that may seem desirable will not compensate.

For example, I would never want to do a longer term sit in a studio apartment as that would make me antsy and it would not matter how appealing the area is, especially since we tend to spend a lot of time at home no matter where we are.

When trying to fill a gap in our schedule, we may end up booking shorter sits and in that case, I would not mind certain things as much since I don’t have to deal with it for a long time.

For example ,we recently booked a week-long sit in a great location with really nice hosts. They were very transparent about the issues and needs of one of their dogs right upfront in their listing, and had this been a longer-term sit, I would not have applied but for a week, it’s fine.

We vary in how far we book ahead–it depends on a number of factors, namely what sits we see pop up. We just recently booked five sits in about a week and a half that range from start dates of the end of October to the beginning of January. We would not have been in any rush to get our January squared away but we saw a longer sit that was really appealing so I applied.

We can easily book sits back to back and any gaps in our schedule are usually not more than a day, maybe two. Last time we paid for accommodation was December.

We typically only create gaps in our schedule if we see longer-term sits we really like and the gap itself is a bit longer too.

There can be a bit of a learning curve with this, but right now, just consider if you have any sort of ‘deal breakers’ such as animals not sharing the bed with you, or strong preferences for certain types of houses, environments,etc… and use that to guide your selection of sits.

Good luck!

10

The advice from KC has got you covered I reckon. You will have plenty of options for US sits. Read some of the threads on screening your sits well, that makes a big difference. I definitely think some type of vehicle would open more opportunities for you.

11

Hi @GirlOnFire :slightly_smiling_face:

I’d say don’t feel you have to solve the whole US travel map before choosing your next sit! We’ve been living this life full-time for going on fifteen years now, and we’ve found it easier to work backwards from the experience we want rather than the destination.

For us, the question is: “What will our everyday life look like here?” Things such as the home itself, the pets, the local area, walks, access to shops and restaurants, transport and the length of the sit can matter more than whether the destination is somewhere we’ve always wanted to visit.

Having a short list of genuine deal-breakers also helps with analysis paralysis. If a sit doesn’t meet one of those, it’s simply off the list and you move on.

And sometimes the destination chooses you. A sit comes up that ticks enough boxes, you apply, and suddenly you’re planning around that rather than searching endlessly for the “perfect” place.

I think that’s one of the joys of THS: the unexpected places can become the memorable ones.

:paw_prints::heart:

12

What’s appealing to you?

13

What’s your deal breaker. We already don’t go out too much. My husband doesn’t like loud resturants and huge crowds. I did make a “bucket list” of home designer to motivate me and dog breed (most I’ve owned and our 15 year old Dobie past recently) to help put myself in the “God Mom” to dogs so we don’t cave and by another for a while so we can travel. That’s why we never traveled, we couldn’t do it to our dobie. I was a dog sitter in our home for years.

Deal breakers list sounds like a good idea, now I just need ideas for that. I’ve watched a ton of YT videos and it’s all basic dog sitting / staying in AirBnB’s for us.

Is it weird to just “stay home” during a stay - I suggested just going and picking one really nice restaurant and one attraction as the goal and he agreed but there’s still so many great spots and great places and we really do have options and tons of experience even on just staying on the East Coast. It’s a lot but give me ideas for dealbreaker. What’s ones that works for you guys?

14

Hi again @GirlOnFire :slightly_smiling_face:

Not weird at all to stay home during a sit! :blush: In fact, I think that’s one of the things we love about THS. We don’t feel that every sit has to become a sightseeing mission.

Our deal-breakers tend to be pretty practical: we want to feel comfortable in the home, have a good connection with the pets, and be happy with the location and the day-to-day logistics. After that, we’re fairly flexible.

Things like whether we need a car, how easy it is to get groceries, whether there’s somewhere pleasant to walk, and whether the surrounding area suits us can make a bigger difference than whether the destination has 25 things on our “must see” list.

And I really like your idea of choosing one nice restaurant and one attraction. That gives you a couple of things to look forward to without turning the whole sit into a sightseeing schedule.

Sometimes the best days are simply coffee, a walk, hanging out with the pets and seeing where the day takes you.

:paw_prints::heart:

15

I’m looking into this now already my mom doesn’t have internet or cell service at her house and she refuses to let me pay $40 for 1200+ speed with Xfinity at her place (even if she doesn’t use it just so I can have cell service out there since we have one car).

16

Definitely, I tired to get him into buying (or atleast) renting an RV to try once and then buy used for a few years before our senior dog finally passed away so we have consistency. I’m trying to see if he will try it out this winter when it gets cooler. Fingers crossed!

17

No. 1 is always a host(s) who understands the nature of the exchange, reciprocity and hospitality, and who communicates well. Without that, no way, no matter what else is great about a listing.

There’s always the potential for things to go wrong with sits, so I ask myself: Would these hosts be good partners if problems cropped up?

Also, I like locations with history, good museums and good food. Clean, tidy homes. A pet or two that I can manage when it comes to breed, temperament and size. I especially like cuddly dogs and cats. Sitting has exposed me to enough cats that I now am crazy for them.

I water plants, but avoid gardening duties and/or mowing. I wouldn’t sit anywhere without high-speed internet or food delivery. And I sit for only one or two weeks per location, because I get bored and I also love nesting at home.

18

A campervan is in essence a converted van made into a home. Much different from a RV. You can usually park it in a regular parking space and some of your hosts may let you keep it in their driveway. Some are selling for over 6 figures but many people buy a used van and just convert it themselves. So many YouTube videos on that.

19

In the U.S. at least, various jurisdictions are limiting parking of camper vans (commonly known as “conversions,” and generally also considered RVs, because that’s a major umbrella for recreational vehicles). That’s because they don’t want people parking in public and living in their vans or other vehicles, which has been an increasing challenge. That’s why there are many videos about people in conversions getting “the knock” overnight, telling them to move on. Police and security people are on the lookout and issue tickets if you don’t move. In some cases, you can get into even bigger hassles.

And note: Many homeowners associations won’t let conversions be parked in their neighborhoods, for similar reasons. They worry that homeless people will start living in their streets.

I did a bunch of research on this before deciding to buy our conversion van (we bought it new and converted). I still follow dozens of conversion content producers.

Even knowing that even conversions can be limited on parking, we bought one years back, because they’re still easier to park than larger RVs. They’re also allowed on more roads/paths in national parks in the U.S. than say a bigger motorhome, because of width and length.

20

BTW, depending on your state and potential insurance providers, check ahead before buying a conversion — some jurisdictions and insurers are finicky about registering and insuring them, because of how they’re converted and people living in them.

In some jurisdictions, conversions are registered as RVs and must be insured differently (usually more expensively) then regular vans that aren’t converted.