As another alternative, you could sell the house, take your $500,000 excluded capital gains as your primary residence, pay your capital gains taxes (both federal and state), and buy your new property utilizing a small purchase loan or even reverse purchase mortgage to make up the difference? 

(Flipper probably picked it up for 20k couple years ago and he was complaining about management too).

It is very important because after that date what you have ROW has to be spelled out like access only or utilities.

And then pick a couple of neighborhoods  maybe a 2 mile be 2 mile block, walk/drive them and get to know what the prices are. 

Then pick the top two or three platforms that will meet the needs of each bucket that you determine you want.

lets see no money down interest only... well that was a go to product in 04 to 06 it was called pic a payment.you get get neg am or interest only or fully amortized you picked the payment. you could do no doc just needed decent credit.. first and second  etc etc.. those loans no longer exist and for very good reason.

They may sabotage the sale by complaining about the HOA or that the cabinets are cheap or utilities are expensive.It sounds like your tenant is a good one so it may not be a problem.

Any investers/real estate agents in that market willing to meet with me so I can pick your brain and compile a pros and cons list???

I want to hang onto this tenant as long as I can since they are literally the ideal tenant however given that they may want to utilize a smaller lease term I need to insulate for vacancy and turnover cost.

That being the case, I'll be spending a bit of time on here to see what wisdom I can pick up.