this is the crux; what is reasonable for a tech worker can be a whole paycheck for someone in the community they are moving to
> how much hassle this would introduce
this is controversial; you are no doubt injecting capital into the local economy, but what are the ultimate consequences?
nyc has a saying: no such thing as a free lunch (the economics always balance out in the end, even if you can't see the scales working)
Example: right now I'm somewhere in the middle of a 90 day stay. We also were somewhere else just before for the holidays for ~30 days, but mostly for vacation. I plan to go back home at the end of March for ~2 months or so to get things straightened out there before then heading out for another 4-5 months afterwards. I've already booked that trip. Usually just as one trip is starting I book the next one for 6 months later.
I travel with my wife so we either book private rooms in a hostel or AirBnB's, though we've been trending away from this.
To be fair, we're both software devs so our salaries together make living basically anywhere "reasonable" depending on how you look at it. We know we're paying a premium but since we can afford it we don't really look at it as unreasonable. Most places we stay come out to ~$2000 USD per month for AirBnB's, and much less for most hostels.
I also keep a cheap studio apartment back in the US for when I'm back for a while, so I don't have to plan where to stay when I'm back. But I know many digital nomads who just use their parents places or another close family member.
Though this is just my experience, many digital nomads I know don't have things planned out as far as we do. And literally just plan things on a whim less than a month out.
This model sounds pretty appealing to me as something to consider doing in the future, but I'm not sure on just how much hassle this would introduce.