yes, it’s all an ongoing experiment!
Personally, I don’t do sits in my family’s area (mainly because a car is needed to get around, and I don’t drive), and I only infrequently visit via sits in my old city (where my friends might have a wedding or something).
If I knew about an upcoming personal event, I would either plan my own stay (non-sit), or if the logistics make sense, I would apply for a sit but include a line in my application stating that on X day, I have a wedding to attend from 13.00 - 21.00, and would it be possible to get a neighbor or someone to walk the dog that afternoon? Some HOs will decline, some might respond favorably but then realize they can’t find coverage for the needed day and then decline… but some will say “no problem” and proceed with the booking.
If I don’t know about a personal event until after I’ve confirmed a sit, then personally, I just tell myself “tough cookies” and miss the event (assuming the logistics can’t work). Recently, I was sad to miss a special family member’s grad party. I missed it simply because I forgot it would be coming up and wasn’t thinking about it earlier this year when I confirmed my current sit. In May, I received the grad party invite and face-palmed as I realized I wouldn’t be able to make it. But based on everything – the care requirements for this dog and the conversations I had had with the HO – I wasn’t comfortable asking to make any special arrangements for a day trip away. (Occasionally, I’ve done sits where the HO proactively encouraged me to take advantage of their friends so I could take a day or a weekend off – but in most cases, if I didn’t ask about it during our pre-commitment conversation, then I’m not comfortable asking for it after the fact.)
Now that I’ve made that mistake, I try to be more actively aware of important events with friends or family that may come up and place calendar holds that should jump out at me when I’m considering applying for a sit during X time period. But it’s tricky, because there are obviously some things you won’t know about until much shorter notice. I don’t have a great answer for this scenario, unfortunately, other than “do your best to anticipate them, and be intentional about what you’re committing to around that time.”
Note also that in my case, I usually have to travel at least a few hours to reach my family. If my current sit, for example, had instead been in my family’s city, then maybe I would have tried to make arrangements for someone to take care of the dog just for the afternoon. Or maybe I would jump back and forth between the party and the home/dog.
I tend to book longer-term sits first, and then book smaller sits to fill the gaps. When doing this, I don’t necessarily worry about getting the long sits’ dates close together. But then, I’ll watch for a shorter sit that perfectly (or almost perfectly) fills the gap. Sometimes, this involves finding one short sit that fills the first-half of my gap and then finding another sit that fits the second-half.
For example:
Let’s say I see a sit that I’m excited about from Jan. 1 - Feb. 15 in Austin, Texas. I apply, and the HO and I confirm and lock it in.
Then, I see another sit that I’m excited about that runs from Mar. 1 - Mar. 30 in San Diego, California. Again, I apply, and the HO and I confirm the sit.
That leaves me with a gap from Feb. 15 - Mar. 1. So now I’m going to save a search that covers that two-week time period in Austin, and I’ll save another search covering the period in San Diego. I might also save a broader search that covers the whole southwest of the US on those dates, depending on what form of transit I intend to take between Austin and SD. I’ll keep an eye out for alerts on those searches, keeping in mind that I need a day or so of transit built-in. What I’m watching for is ideally a sit that starts on Feb. 15, 16, or 17 and ends on Feb. 27 or 28 or Mar. 1.
Maybe I find a sit that appeals to me in Austin that runs from Feb. 15 - Feb. 19. I’ll probably apply and (if we confirm it), I’ll reconfigure my search settings to try to fill the remaining days. Or I might wait it out (especially if it’s still far in advance) and keep watching for a full two-week sit.
As the “remaining dates” timeframe gets narrower, it becomes more of a gamble to try to land a sit that fits perfectly. Sometimes it works, and sometimes it doesn’t. But I try to gauge likelihood of a match by how far out I am from that date and how many sits are being posted for that location, duration and time period.
Also, keep in mind that it’s easier to get a one-month sit than it is to get four perfectly back-to-back one-week sits. In other words, longer sits reduce the planning hassle.
Just my two cents, but this rough approach has been working for me so far! 