I've looked into turn-key companies but the cash flow seems to be barely there or dangerously creeping toward the negative after accounting for all expenses.

New properties have fewer problems (no deferred maintenance), a 1/2/10 warranty, and yield higher rents now and in the future.

He trimmed the bottoms but refused to do the tops as it was too time consuming and dangerous.  

I know all these things are minor, but wanted to know if I had tools for negotiations, because they can sound big and dangerous.

We have enough equity in the apartment to do this several more times if we can find deals (I too am investing in a relatively small community, so deals are fewer and further between).Sounds very similar to what you're doing. 

If you came to me and asked for that deal, I would accept it because it is rare that I have a vacancy for more than 30 days.The danger?

The other potential problem would be a lot of bases, as you know, are the only thing in some of the cities and if something were to happen with the base, it could be dangerous for an investment property nearby.

I would be cautious about your plan for 'long term' AirBNB' with family as that sounds dangerously close to mortgage fraud which would not be good for your future real estate needs. 

He definitely has the money and is willing to pay points, but just thought fewer points and a higher APR might be attractive to somebody.  

Now of course being Alameda that portfolio was worth a lot back then  probably 100k a door and today probably 200k a door LOL.. he was a cranky old bird.. and the ranch I sold him I really wanted that one... it was really cool.but the take away is if you take this on as a JOB  like your doing any of this stuff will work.were the danger comes is those that think they can do it from afar or they just don't have the stones to deal with the people and the issues.