I have come to understand these are very challenging places to find a potential Airbnb due to both local regulations and HOA/insurance guidelines.

Few data points :FICO over 780DSCR over 1.25 (some over 1.4)LTV 75% Loan amounts ranging from 56.25K to 200Klooking for PAR loans (no buy down) under 7.75%Thanks Sharon, min DSCR loan is $75k - if you have multiple properties you’re going after you potentially put them into a blanket portfolio loan.

An obstacle I'm running into with building my portfolio after analyzing a potential deal is the very high property taxes, particularly on properties that have been owned a long time by the previous owner.

I am actually looking at a potential 3rd property now that would be a rental.  

We saw the potential and were their only offer.

Number 1, consider going the max amount of $766.550, the reason being your potential rent income will be that much higher. 

How best should I go about presenting him a potential owner finance deal at a fair market value on one of these properties that would be ideal for both of us?

I would be happy to chat sometime about potential ways of getting started.

Keep doing what is working AND expand your sphere of influence while you cast your vision to potential partners.

I’d no longer have to worry about unforeseen issues or dealing with potential bad future tenants.