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.

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

For the most part its just health and safety items, which are items we should have remedied anyways.As someone else mentioned, biggest thing to avoid is having the house tagged as vacant which the city will do if it sits empty for too long (handful of months, grass not cut, etc).

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. 

He has no safety net so I don't think its wise to take the risk because if he did a deal, lost disability and then since hes brand new to REI lets say it takes a while until he gets his next deal I just want to help advise him best!

The advice is very basic.

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

I do plan to buy a property with 30% to 50% off and have it "acts" as a margin of safety.

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.