@globalpetsitter, kudos on becoming a digital nomad. The housesit community is surprisingly diverse in terms of situation, objectives, preferences. There seems a hearty niche of full-time sitters and/or international travelers.
UK/Canada passports. Over last 2+ years, we’ve completed approximately 50 housesesits (majority THS). Sits broadly one-third each in Schengen zone, UK and North America. Several of our sits have exceeded one month duration (longest three months). We are fortunate to housesit with an experiential objective - so destination/journey is a key decision criteria.
Re where to sit, we’d encourage that you become familiar with the ballpark profile of THS listings (thread below has data - easy to update via Search function on THS app). This may reinforce opportunity via THS but also limitations. For example, we’ve been exploring idea of using THS to spend months in South America or NZ/Australia but listings are alas few (and some listings have more pets than a zoo!). To aid some future life planning, we have partly used THS to visit some places of specific personal interest.
We’d encourage that you experiment and gain experience with THS Saved Search tool. We find it fabulous. We set searches for specific destinations and, once in a while, opportunity presents itself.
Re visa implications, there’s a whole lot of content on this topic. Various countries consider housesitting as employment with in-kind compensation. But few countries enforce. We’re not going to give related advice as each person determines their own risk appetite. We are currently comfortable to visit anywhere other than the US.
Finally, we try to balance responsibilities. We do love dogs - woof! But they can be demanding. So we try to actively switch between dogs, cats and no pets.
Good luck on your adventures. Our journey has evolved as we gained housesitting and perhaps a better personal insight.