Tenant 2 on the other side has supposedly been living in her unit for 20 years, and she currently has a roommate.

So I am not the smartest person and some of the helpful replies in previous posts was above my mental capacity.My situationI own a home (homesteaded in FL) and have 2 roommates which help pay the bills.numbers - mortgage left 155k, home value 330k, current interest rate 4.125% on conventional with 24 yrs left on a 30 yrmonthly payment with HOA $1600 pcmI am wanting to either1) turn this primary residence into an LLC and purchase another property to move into and start the process again with the aim being to rent my current house out on an annual 12 month lease for at least 2 - 3 years as I was told that as long as I lived in it 2 out of 5 years I can then sell without paying capital gains (though this confused me and anyone wanting to teach this to me like im 5 years old would be greatly appreciated).

My goal is to live in this first property for at least 12 months (but realistically a few years) and have a roommate in the second bedroom to help offset the net costs.

If you don't mind roommates, house hacking also works.

People over 40 consider having roommates when starting out in life to be normal. 

Being a college student, you could house hack a single family if you wanted to have roommates, or you could house hack a multi-family. 

I plan on living in this with roommates for 2 years and going onto the next deal.

I plan on living in this with roommates for 2 years and going onto the next deal.

A rent by the room or roommate strategy is great for expensive markets, making it more of an equity and cost reduction play for the long term.

I agree that it's harder to manage by the room logistically (roommate dynamics, common area cleaning, etc) but it is allowed.