A good bookkeeper/financial advisor can get you setup with automated processes to make sure you know exactly where you stand for each property and show where every dime is spent. 

@Cisco Hood, not enough information to calculate a true financial decision.   

However, I want to provide security for my family long-term and attain Financial Freedom.

I stumbled upon Bigger Pockets 2 months ago through a Financial Literacy blog that I follow and have been an avid listener to the podcasts, which led to peaking my interest in RE investing.

This scenario played out with a lot of my family who moved to Florida and wanted to come back because of the fear of future weather disasters and other issues.

It is helping you weed out bad tenants.If they are not financially responsible enough to save that tiny amount of money they are just a breeze in the wind away from not being able to pay the rent.

If you go this route you'll need some pros on your team - a Qualified Intermediary for 1031s, a tax man, and fiduciary financial planner to help with the ins and outs of the trust.

I ran the numbers on a condo I own and I realize it is underperforming financially compared to a home I recently bought.

Anyone who works for a financial institution can be a certified mortgage professional, which means they never got training in mortgages, and don't even know when they are breaking laws. 

However because of my age, and financial situation every agent I have met with or contacted ignores me, never responds or fades off and just forgets about me because I can't afford to buy a 300k house.