You don't say your age but as you are in college that would make me think late teens early 20's but you never know. 

Vacant properties in this area just get terrorized by teens and we are not sure how we could secure the property more even if we put bars on the windows.

These options may not make it sexy for you personally, but they can give you an opportunity to get in the market.

This certainly isn't as "sexy" as owning a bunch of properties on your own that you have full control over, but I can tell you after doing around 10 of these deals and having a few go full cycle, it is definitely sexy to make money passively without having to do anything. 

As a teen/college kid in FL following a hurricane I made a ton for cleanups in the 2-3 weeks following an event.

You state he's been a model tenant for three years but perhaps the mix of housemates age and sex is the real problem, this is why I mentioned how you structured the leases and if you are matching up the tenants. 

It rings true in lots of asset classes (not just real estate), that "boring is better" which is true because the more interesting/"sexy" an investment is, the more competition there is and thus lower returns. 

I feel like a lot of my consulting clients ask about making the change because it's the new sexy investment model but they already have a great, hands off long-term rental and the switch to a midterm rental or furnished rental doesn't necessarily make sense. 

As a high school student, your first step is to read this book from Bigger Pockets. www.biggerpockets.com/teenIt is specifically for teens who are exactly where you are right now - the beginning.

If you're looking for the sexiness of fixing and flipping, stick to reality TV and keep telling yourself "that looks easy, I could do that."