The majority owner should be required to sign reps & warrants at closing to be personally liable for them.You didn't mention checking the plumbing - hidden plumbing leaks can cause more damage over time than just about anything else!

Can you take the small profit which may qualify as "tax free" and invest in properties on the mainland, or in a retirement account.

Then find out if rules were to ever reverse, do the CC&RR's have a clause protecting existing rental permit owners so they are grandfathered in despite any changes in the future.Also, check the OTA's to see if anyone in this desirable lake location are advertising their 30+ day rental.

If you're applying for a Conventional/FHA/VA/ or USDA loan, then they will do a "global cash flow" where they take into account your PITI (Principal + Interest + Taxes + Insurance (hazard and flood) on all properties (second mortgages included), HOA payments, car payments, student loan payments, credit card payments, and installment loan payments in the numerator and your gross income in the denominator.

You always want to make sure the guest has actually paid before sending check-in instructions.

Also check out the various meetups on Facebook or meetup.com.

Regarding entity structuring, that's a conversation you'll want to have with your accountant and attorney.

@Julia Trudeau,Virtually any retirement account can be self-directed.

My network is large and any referral I give is someone I trust with my own legal, accounting, inspections, financing, etc. 

If you check their websites they may give local agents contact info.