I am happy to speak to what I have seen as the most common set up from a tax perspective to give you a starting point for a deeper discussion, but ultimately you will want to speak with your CPA in conjunction with an asset protection attorney because this requires a deep dive into your specific situation.  

I'm wondering if he would be willing to accept an offer that has long term tax benefit, I would give him his asking price, the only real problem I foresee in the repayment would be another big downturn.

Nor would I buy here with the looming property tax threat against STR's. 

I have been investing in residential real estate since 2012 first in California and then in Florida.My cash flow has been slowly and regularly increasing during the years thanks to the cap on property tax increase in these 2 States (IE proposition 13 in CA and 10% cap on investment properties in FL).Recently I started to analyze deals in Texas and Indiana for my next rental property.Reading some posts on this platform and talking to some investors, I quickly realized that, during the years, all the rent increases will be eaten up by the regular property tax reassessments.I think many investors often underestimate this issue.Am I missing anything?

The taxes & Insurance ( combined) have gone up $200 a month since the lease was signed.

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

Other kinds of liens jump ahead in line such as IRS tax liens, property taxes, municipal utility liens, etc. 

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

Duplex is empty with a few hundred in back taxes, triplex is 2/3 rented way below market.

We're willing to kick a bit in each month but every multifamily we run has us paying close to full rent after insurance, taxes and expenses.