Anywhere from small contractors, pest control, welding, even crossfit, etc.

We are self performing the entire build with exception of mechanical sub contractors

That said, if you've been a landlord for years and have niche relationships with contractors / roofers (or do the work yourself), then it would seem you're in the ideal position to make this decision. 

Obviously, your son's preferences play a huge role in what he will enjoy/be drawn to study. 

I ended up sending the tenant a 24-hour notice and went in with a contractor.

Begin by giving contractors smaller projects and gradually progress to a full BRRRR.

When I was a full-time wholesaler most of clients were able to pull the trigger within minutes of entering the home, some trusted me enough to buy sight unseen on my recommendation, and some always wanted to get a contractor in there or run the contract past their lawyer.  

You guys might just enjoy yourselves.

Did you have people like a real estate agent, contractors, bookkeepers, a CPA, and all of those other roles already on your "team" or did you just purchase the first property and find people for those roles as you went?

Rochester is great for investment and the prices are decent to get a duplex (4 bed, 2 bath min total).One concern though, when people who are not contractors say they are good at home improvements, they aren't usually as good as they think and their value isn't higher, it's actually lower because of unpermitted renovations or personal cosmetic choices.