Sounds like there's a reasonable chance he'll save you more time/money/headaches than his services would cost.

Theres a good chance that the college will be buying the whole block in the near future.

4) Any chance insurance covers gas leaks?

A list of only 64 is hardly a chance at success but, guess what, it can happen >>> with repeated mailings.

What are the chances of the property increasing in value in the next few years?

I personally know of a very active investor, he is a friend and business associate (not the one you are referring to, although chances are I know him too) who did exactly what you are describing.

There is a good chance my family will be there 5+ years.

I came upon Bigger Pockets by chance, but since I've been reading, listening, and learning a lot.

There is a chance that the borrower would willing to refinance out of the Note.

Which is like someone with a sword not having much of a chance against someone with a gun.