I’m a tradesman that works for a contractor and have 20years experience in Reno’s and new builds.

Is it any harder now to find a deal or is it the same as always, just a different group that learned that real estate actually does require work?

I definitely would love to hold onto them, but with the stress of school, I would rather not have to worry about the overhead of the properties while having no income.

It is way toomuch hands on and working with Airbnb and VRBO was terrible due tothe huge language barrier.

Welcome to the community.I am a real estate CPA who works with investors and real estate beginners like yourself.

I understand that might not be a great rental but in Jax I should still be able to make it work with the difference in payment for the new property as primary.

I work with a bunch of contractors, i'll shoot you a PM. 

I will send you a PM with her details.If you do not use her, I would recommend in general to work with an insurance broker rather than an agent from a large company like State Farm or Geico, etc. 

I have recently came across some videos on working with Section 8 on rental properties.

(A good example of why you should work with an STR-friendly agent who knows Airbnb laws in and out. ... ;))Anyway, what OP is looking to do is legal in Littleton.