You mentioned wanting to meet up with folks that like doing outdoors stuff.

Unless you've got something unusual <$500.I'd be looking for stuff like:1) Major CapEx - Life of roofs and siding and paving and plumbing2) Moisture invasion ANYWHERE since this gets more expensive the longer you wait3) Making sure stuff (like remodels and wiring) is up to code. 

Start with the "easy" stuff like browsing Zillow and getting yourself a great agent.

Exciting stuff, but I'm unsure how to proceed.

This is all pretty normal and routine stuff. 

During good times, they move from site to site and need a place to keep their stuff.

So, yes, the lender will underwrite your property and base their decision on how they think the property will cover your debt service, but they also want to know you have the ability to step in if stuff goes sideways.

For my wife and I, we have little interest in trying to find personal happiness through buying stuff.

Hawaii is pretty strict on that stuff. 

What was interesting is that most of the protocols were obviously intended for hotels and there were pages and pages of stuff hotels must do.