.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

To minimize capital gains tax on the sale of their primary residence, your in-laws can utilize the $500,000 capital gains exclusion, potentially explore an installment sale to spread tax liability over several years, or consider converting the property into a rental to use a 1031 exchange for tax deferral eventually.

This is where I'm very inexperinced and don't understand what is standard for industry or what could potentially bite me down the road.

The opportunity cost of losing potential market gains in your retirement fund should also be considered.

Alternatively, restructure the loan with equity participation for potential capital gains treatment at lower rates.

Assume a couple of months of vacancy, consider potential unexpected repairs (like HVAC or plumbing issues), and test the numbers with rents dropping by 10-15%.

So, they could potentially buy another house later on.

Richmond certainly would have some potential in pulling trades from, but coming from Lexington, you might face an added trip charge on top of the service provided.Over the past few years, rents have increased nationwide.

Also this could be a potentially lucrative business partnership.

Here you would have to put it in the MLS if your are with NAR, but it wouldn't syndicate out to all of the public sights, and you can send it to any potential buyer that you may know.