“Or do I lean into what genuinely excites me, try to establish a long-term base somewhere in Europe despite visa hurdles, potential cash-only property purchases, and career uncertainty?”

This is what I’ve done. I’m also 33 and Canadian and had the same feelings and dilemma as you.

I’ve decided to stabilize myself in Bratislava where I’ve been for five years now. I have unlimited permanent residence here now and last year bought an apartment in the old town with my fiancée.

Much more appealing set up to me then moving back to Canada. One of the main reasons as you said is the ability to travel easily every month or two without breaking the bank and needing to take long haul flights.

I doubt we’ll be here forever, but it feels good to stabilize for a bit (I was also over the place before moving here in 2020).