The numbers speak for themselves, it looks like a solid deal, if the Numbers are true. 

I would look at how I can bring my reno costs down while keeping the quality at the right point.

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

I'm a newbie just starting to speak with lenders in Milwaukee.

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 want to be confident that I am speaking with the owner.

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

Ask to speak with some of their current owners and current/former tenants.

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?