Slow travelers (to avoid the whole "digital nomad" thing) are, in my experience, most welcome, especially in family-run places: We are pretty low maintenance.
> Any advice on easing the stress of finding the next place?
This is how I do it: Book flight and one or two nights in a hotel (depending on duration of flight/expected jetlag). Find a better hotel locally (one I am comfortable paying and staying at for the whole stay in worst case), start local hunt for a place. I usually find something within two weeks that is a much better deal than anything on airbnb (or with any other online presence).
These two weeks allow me to learn the very basics to make an informed decision: Local salaries in the area (if a cop makes $200, a lease of $800 should ring an alarm), reality about security issues (pay more for something in a gated community?), actual transportation costs (just because a taxi has to be metered by law, it does not mean it will be for you, if you stand out as a foreigner) etc.