I would focus my attentions here and try to stay local (within a 4 hour drive) as the POH rentals require more engagement.Financing is a tough deal... but sometimes you can find those Mom and Pop operations with quite a few POH rentals that will work with seller financing on a reasonable interest rate with a balloon within 5-7 years. 

For another business I run I do post daily accountability in a FB/mentorship group and that does help me stay on track.

We want to get a Vacation Rental Permit for stays under 30 days for ADU but current zoning doesn't allow it.

One of the greatest, most important lessons has been, staying in my lane!

He bought a home for himself in Lodi California but work in the Bay Area long story short he can’t deal with the commute anymore and decide to stay with a buddy close to work.

But if they don’t even bother to fill out the forms to apply, or get a basic job to make ends meet, or borrow money from family or friends/ somebody else besides you, then they can’t stay.

I have considered it but I keep things at a flat rate for the exact reasons you stated.I want people to get the exact price when they stay at our lake house.

Staying flexible and partnering with a skilled property manager or agent would be key to achieving long-term success.Good luck!

Tenants prefer detached housing over attached housing and stay longer. 

Over the next couple of years, I don’t plan to use the property often, but I may stay there occasionally when it’s not occupied.