Every person who gives you their contact information should be placed into your database.

What are their nightly rates, occupancy and amenities?

As @Jonathan Greene mentioned this is kind of a dated strategy in the new price/interest rate environment.

As for your Index funds, if you were trading indices such as SPX, you would have the favorable tax treatment accorded to §1256 Contacts:  60% of gains are Long Term Capital Gains, and 40% are Short Term capital gains.

it makes for a very juicy internal rate of return.

Conventional loan, 25% down at ~7% interest rate How did you add value to the deal?

So you are better off finding someone who wants to rean interest on their money and getting a promissory note signed and giving them a 10% interest rate and having them give you a 15k loan interés only for a 12-24 month period.

If I do contact him, what should I say?

In the end, it cancels out any benefit.Loss of Key Homeowner BenefitsIf you sell your home to an LLC or S-Corp, you’ll lose:$250k/$500k capital gains exclusion on selling a primary residence.Homestead exemption on property taxes.Owner-occupied insurance rates, which are cheaper than rental insurance.Substance Over FormIn tax law, the IRS looks at the substance of a transaction, not just the form.

Higher rates and tremendous demand for inventory by both owner occupants and investors have resulted in an inventory shortage all over the US - in Oregon and in Ohio.Hope this gives you some things to think about.