The headaches you get from a bad section 8 tenant can outweigh the benefits by a long shot.

Money in hand sounds great, but my portfolio strategy (even though it’s currently small) is long term buy and hold.

Given that he's got a long history in business but is struggling to cover $30k in Op-ex and marketing spend, my guess is that this is either not very well managed or is in distress.

There are a few ways to go about structuring the loan for you on favorable terms. 

The house likely won't cash flow as a long-term rental once you move out, and you're spending more money upfront in both monthly costs + downpayments and closing costs. 

She sent me this long formal letter asking me to change her annual lease to month to month because she is seeing roaches in the unit.  

So as long as the demand is there and the boundary is never expanded (which is very unlikely), then the supply is so low that real estate there should essentially ALWAYS be in demand.

I apologize for the delay and I hope your deal went smoothly.William, the only way I see that being possible to get someone to lend is if you have very strong contingencies for the return of EMD that stretch the full term of the contract, as well as a personal guarantee on the loan amount. 

We have had a Strctural Engineer out to the property and while we don't need to conduct repairs within the next 5 years or so, we will need to address both of these things at some point and it will likely cost us about 100k.Any advice on selling or holding for the long term?

I am wanting to invest 100% into real-estate whether it is flip and sell and/or long term rentals.