Also at 15 you can work and make money when not at school.

I also see people in your situation who as a newbie do okay, that's all I'm gonna say about it and you can take what you want from that because I don't have the Magic Pill to give you to make this work.

Big thoughts are I'm 43 and can retire from my W2 career (Middle school principal) in 10 years, and I want my investments ready and waiting on me then.

Go visit Disney Springs, walk the resort properties, go to Magic Kingdom and Hollywood if you can.

Unless you understand what's going on and why, its like having an elementary school student drive your car to school.

McKinney schools aren't that good. 

The magic of STRs is that any amount of tax losses generated by STRs, including of course losses from depreciation and cost segregation, can offset your other income, and you don't need to qualify for REPS. 

We are in a small Midwest college town (MAC school) of about 60k people.  

School system?

Also, if you're renting by the room, it’s a great idea to try and be near a school or university for demand.