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

I lived in the Poconos many years ago when I was a kid and the same STRs that are around now were around then, only they weren't called STRs back then.

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. 

The advice is very basic.

Acquires a new one via capital injection annually, and with the pyramiding, after 20yrs of this will be siting on a nice holdings that is planned to fund kids university tuitions via rents at that time, which around yr17 we will start deploying into assets with more of that cash-flow focus. 

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

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. 

Part of that you can justify because of the necessary repairs, but overall higher price points appreciate differently.The median home price has basically doubled in Milwaukee from about 160k to 320k in the last 10 years.

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.