Here’s the TL;DR of my long response:
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Dream first: Map out where you’d love to spend the next two years (e.g., 3 months Thailand, 2 months Sweden).
 
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Check the rules: Research work visas, tax obligations, and housesitting rules using official sources (embassies, gov’t sites).
 
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Adjust the plan: Tweak your itinerary based on visa limits (e.g., Schengen 90/180 rule).
 
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Budget realistically: Make sure the trip is affordable without housesits, since sits can fall through.
 
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Set saved searches: Once your plan is solid, create THS alerts for your chosen places and dates.
 
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Be patient & disciplined: Wait for sits that fit your plan—don’t derail your year chasing tempting off-route listings.
 
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Stay flexible: If a sit doesn’t work out, fall back on your budgeted backup (hotel, rental, etc.).Welcome to this exciting world!
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
And now - for the very lengthy version that goes into detail about the above, should you be so inclined:  Though this isn’t precisely what you asked, I think my best advice is to plan your next two years as though housesitting is not an option.  Dream a little dream and think: Where would I love to go? What would I enjoy experiencing?  Map it out, plan it out.  Maybe three months in Thailand? Two in Sweden?  And so on.
Then and only then - after you’ve dreamed your dream - go back and start mapping out the practicalities.  Since you are working remotely, you need to understand work visas as well as housesitting rules.  Not to mention taxes!  Taxes generally follow the work , not the company.  One year I had to file taxes in five different countries (really!) because I was in each one just long enough to have to file there (luckily my company, whose fault it was that I was in those countries, paid an accounting firm to do it for me). So many people think, incorrectly, that if they work for a UK company they only have to file in the UK. NOPE.  I personally know two people who learned this the very hard way, one of whom ended up in bankruptcy (and a divorce) as a result.
Use an official channel, like an embassy or a country’s government website, to find out “what’s what” for digital nomads.  For example, I was able to work in one country for 30 days with no work visa, so I left on day 30, but in another I needed one on my day of arrival.  Ignore the advice from scofflaws who recommend trying to skate by on a tourist visa or lie to authorities.  You are in your mid-thirties, and having a black mark on your immigration record will do you zero favors in your long and vibrant future.
So:  Now that you know the practicalities, adjust your dream accordingly.  Maybe you wanted to spend two months in Sweden, two in Germany, and two in Spain, all back-to-back, and now you’ve discovered that as a UK passport holder you can’t do that without exceeding the 90-day-in-180 Schengen rule.  Plus you’ve learned you’ll need a digital nomad work visa for Germany but not for Spain.  Possibly you can modify your plan to go from Spain to Thailand to Australia and then back to Germany, giving you time to get a work visa for Germany (they have freelance ones if you’re a freelancer).
Now.  Now that you’ve mapped out your two years, and you understand the visa implications, and you’re getting excited and you’re confident that you can afford to do this even without housesitting:  NOW is the time to set up “saved searches” for sits in those locations and at the times you plan to be there.  This has worked a treat for me.  90% of the time I have found the perfect sit in the perfect place at the perfect time.  I had to learn to be patient - so patient.  I’d plan to be in Dallas but a juicy sit would come up in Chicago.  Switching to Chicago would throw my entire year off track (I once gave in to the temptation and it ended up costing me far more than it saved, both in stress and in money)  So I’d hold my breath, wait for my alert from my saved search, and pray.  It almost feels like the Universe must be a THS member because so many times I’d get a sit for exactly the dates I needed.  And the few times I didn’t, I’d just get a hotel - remember, always pick places that you can afford without THS, as sits sometimes fall through at the last minute.
THS has been an absolute dream life for me.  But I plan my life first, and see where THS fits in with that - not the other way around.  Having a plan in advance helps in other ways, too.  Often hosts ask if they can use my services again, and by having a plan I can say, “Well I’ll be back in the area for two weeks in October of 2027”.  Multiple hosts have scheduled their vacations around me, which is not only gratifying but also simplifies trying to secure sits in the future.