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.

What I don't understand is how should I think about the tax benefits when holding rental property in an LLC.

Tying up the property with no payment being made and property taxes accruing for 2 years is not uncommon.  

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).

I have done this once before to  purchase our condo with no issues and we both make more than enough money to pay both the new mortgage and pay ourselves back (85K + 3600 after tax monthly retirement for my partner, and 140K for me).

I'm trying to figure out a structure that would allow me to essentially pocket the $100K rather than applying it to debt.

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?

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

That does NOT change your personal liability for the debt.

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).