I'm not trying to be rude, just curious as to your method as it doesn't make sense to me.

The products will always speak for themselves and I aim to never stray from delivering such a high level of quality rehab. 

If you wanted to keep your current VA loan (which probably has a pretty good rate) and get a $30k HELOC with a $20k draw that would be the best (and only) method of doing something close to what you described. 

I've always been a people person, and I think I have a lot of qualities that would suit me well as an agent.

I still work the day job but in a government role for quality of life.

You hire him based on your confidence that he can do the required job, at your level of quality, in your time frame for a reasonable price.....that's it.If you think its a good idea to hire the desperate and overly friendly, one leg guy on pain meds living on his boat waiting to sail off to wherever he wants, then by all means do it.....no red flags there.....The job you are looking to do sounds pretty basic......so it may be worth a shot....doesn't sound like you will be out of a lot of $$ if it goes southBut I would pay based on the job (not by the hour) and buy the materials myself and only pay as the work is done

Are there lots of quality tenants out there looking for rentals? 

Still working on the plea win-win method.

The school quality was one factor that narrowed our choice of property significantly and it also made it much more competitive to get a deal.

I've spent a lot of time on the forums learning and don't really have much to contribute, but I can say in that time, I've identified the small group of folks that I really value perspective from and the larger group of people that are selling something, argue to death that "their method" is the absolute best or whatever.