Don't think it's worth it for 1 property.Vrbo and Airbnb will sync calendars with each other and send basic messages already.Vrbo has free built in pricing tool.

Sounds like the house is basically New just needs a new tenant once this one moves out and then there's plenty equity in the deal. 

Start by learning basic metrics like cash-on-cash return and cap rate, and check out resources that dive into rental market analysis.

You’re able to learn the basics of a real estate investment with lower risk and build equity at the same time.

My basic philosophy is that if you can't handle the little things, then you can't handle the big things.

Many properties in Macon lack central heat and air which I feel is a "must-have" amenity in GA.

I would start with the basics first.  1.

Another thought you could just keep the tri-plex and gift them the net income each year...it's basically the same thing without any transferring. 

He was basically Someone that was in their early 20s maybe a relative to someone in the coaching company.

For example - you're starting a $100,000 remodel on a propoerty that you have acquired, the Scope Of Work includes basic lipstick stuff like a kitchen remodel, a bath remodel, and new flooring and paint.I would start with a draw of no more than $10k, that is more than enough to get anyone going and it shows your good faith.