Thats kind of the beauty of thes exchanges.. you get to reposition your capital, ideally in a property that ticks more of the boxes you need.Now, thinking about older buildings.. some folks underestimate how well older properties can hold up if they’re in a good location.

What @Mackaylee Beach said....at least have this guy fill out an application and check his background (and charge accordingly).

I charge a good bit for my properties, that screens them.Do hotels run background checks on guests?

Full background checks.IDs, names of all people to occupy house.All move in money received, no personal checkslease signed by All.Walk through inspection completed and signed.

The beauty of this is that intermediaries who work with me know that I make “fair” offers based on VERIFIABLE facts, that I follow through with completed deals unless important information was with held or information provided was false, and that there’s absolutely no value in presenting deals to me where the seller/borrower/investor is unrealistic, naive, or otherwise wanting to “test” the market.  

It is a very well established market with solid, steady revenue, and it is beautiful to visit.

VRBO does not seem to do the same guest verification or background checks as Airbnb and you have to opt in to Damage Protection (insurance or deposit) which I've read can detract people from booking.

But, in the end, a HELOC is great to just have in case that beautiful day comes where I get a great opportunity.

Would you say your perception may be different from most people because of your accountant background?

I would suggest a good PM to start if you don't have a solid background in hospitality or at least something in the service industry.Self-managing can save a ton of money if you know what you are doing.