I whip out big project estimates in a few hours compared to a few days.  

He's the guy who shared my interested and connected us, he wouldn't recommend him as a seller if he had bad experiences with his other properties.I did ask about other properties and he shared about a duplex for $200k, but I wouldn't be able to afford the down payment needed.He acknowledged the rent is low compared to the market and never mentioned that it's his "best" property.1) Agree, but if he's been a good tenant is that necessarily a problem?

Its pretty much a necessity as the loans are so large on average compared to other areas of the country..

How is my property performing compared to the local market? 

A property doesnt increase in value just because an STR is run successfully on it. its value on paper is based on the comparables in the area.

We're exploring creative ways to provide him with the cash needed for the down payment while avoiding triggering a taxable event.One strategy we're considering is purchasing his future primary residence ourselves, making the mortgage payments, and then, once we've built enough equity—comparable to the appraised value of his rental properties—transferring the title to him as a form of exchange.What are your thoughts on this approach?

Will post back how long it takes and the “compared to what” responses as it happens. 

Compared to fixing them both up and paying full taxes as flips.

The "fair market value" parks they compare us to is not even close.Regarding our park, in NYS, the owner is responsible for moving the home off the lot in cases where we are evicted (to somewhere it can be put - the company then could charge storage fees if the owner wanted the home moved to another site) i, that is state law as we own our home and rent the lot.

Property Valuation:Investors look at a variety of factors to determine a property’s value, including comparable sales (comps), rental income potential, and location.