If you want to get some of the "guilt" of your shoulders, you could rent to Section 8 tenants.

If he gets paid hourly, or as a GC, then gets a bonus when things go well, you have shouldered all of the risk.  

I use Chicago control thermostats, they don’t allow the heat that i am paying for to be set above 71 and they auto set back at the appropriate times... has saved me a fortune and I don’t have to pay for building WiFi or make a tenant feel like I am looking over there shoulder. - Very smart device.I use wired doorbells.

Shoulder seasons can be very slow so need to factor that in.

It's good for busy professionals because the maintenance and repairs are the responsibility of the tenant so everyday property management and expenses are not on the shoulders of the investor.

What would be the point of checkbook control if someone had to look over your shoulder all the time?

Part of that system is having a Development Agent who’s looking over your shoulder to keep you on track and from making costly mistakes.

In a few months/years, armed with knowledge, you will be in a better position to decide what is the best fit for your needs.You sound like a smart guy with a great head on your shoulders.

@Ryan McDonald My concern about places like that are shoulder seasons.

Quote from @Ralph Noack:We all make mistakes.It's not wise to shrug your shoulders and continue making them.1.