Maybe think about selling it and buying another place --on the water--with a dock and a boat launch, plus a new speed boat.Lots of new experiences, water ski-ing, fishing, hiking a new area, etc..Buy small, with big land and add on to it every 3 or 4 years.Some extra bedrooms, a bigger patio, a hot tub.Have contractors do the work when you are not living there--so its ready to go when you arrive.Invite everyone in the family to take vacation at the same time and stay there all together (collect some $$$ to cover their food costs if that bites your wallet too hard).Have an adequate well and septic field to handle a lot of people.Just my 2 cents.

He has the choice of not living in these environments and also leaving the current property... but are there any options for affordable housing that are regulated and safe?

Or is this just a lesson that this strategy is only worth it in a very low interest rate environment in a low price market? 

We have them the 2nd and 4th Thursday's of the month and they're a free, no pitch environment!

Take advantage of these as it's in my opinion the best way to get around others who are already in the mix with most Meetups being very low-pressure environments!

This still works in a lower interest rate environment.

He's harassing the construction crew and my on-site person is ready to take him on a one-way fishing trip.

If you are flipping that is the best way to do it. if you are holding, you may find refinancing challenging if STR financing dries up due to the current banking environment.

If you give a man a fish, he will be hungry tomorrow. 

In today's environment, I wouldn't work anyone who was not covered by WC.