Where do you live, and where are your units? 

I currently own a 1 bed 1 bath single-family house as my primary residence.

I plan to move down to Miami to be closer to more investors and a better quality of living.

However, it's a deal in a different state and during the Facetime showing, I could tell the tenants were gross and makes me think they don't care about taking care of the place or their living conditions.

Currently have a great job but want to start acquiring  2-4 unit complexes.

Hey @Spencer Cuello, so you will find most of us aren't fans of arbitrage.I see you listed NYC so you know that you can't do a STR in the city unless you live there.IE: You need to be onsite, living in the same unit you are going to rent.As per usual...

Currently, we own one vacation rental in Duluth and one college rental. 

For the son to qualify for the $250k exclusion, I believe he would most likely need to meet the ownership and use test, meaning he needs to own and live in the home as his primary residence for at least two of the last five years before the sale.

I have about $80k in a HELOC on my current home where I live.

Quote from @Kyle Barnhart: I live near Phoenix and looking to invest locally.