Full disclosure - I knew John back inthe late 1970s early 1980s when he traveled the guru circuit of those days as guest speaker at REI clubs selling “books and tapes” at the back of the room.  

Fortunately its a pretty small roof. 

Fortunately it had a rent point in a different stratosphere than your depicted rent income and could absorb crazy high insurance increases.

So happy for this young man and his young family.One of my bizz partners years ago and mentor.. ( he was President of a fortune 500 company) we belonged to the same country club in Napa.. him in his mansion on the Hill me on my house down in the low lands..

Hiring someone to do the work will likely cost too much (I would charge a small fortune, it's an incredible amount of work) and doing things as cheaply as possible will bite you in the *** later when you start having issues with your own shoddy work and/or materials.

its a fact those buying into Paces club for the 8 to 10k 90% will do nothing but Pace has retained the payments.. 

Fortunately, the seller was cooperative and patient, and we only lost about two weeks in the process.

Which I'm assuming is similar to fortune builders where you are shelling out 20-40K for guidance.

I also have my member-guest at my country club. 

I recently sold one I had on Seabrook Island because the club/regime/HOA were frequently changing the rules and making it harder to operate smoothly.