If they're on disability and don't have a job or a large volunteer commitment and they're not obviously physically disabled, get a full confidentiality release of their mental health history so you can determine if you can cope with having them as a tenant. 

Run your contracts through a local lawyer (I can refer you to mine if you message me directly) and do a better job of letting the seller know what you plan to do with the property.

Do I still need a normal w-2 job  or can I live and grow exponentially from $200k? 

In terms of living on the income my real estate generates (I have a job but not a very secure or reliable income job), would I be better off staying with the properties paid off or looking for similar good deals and mortgaging them ?

Debating getting my real estate license while working a full time job.

I would not be able to put in the time to research deals, and do all the ins and outs of real estate investing that make it a second job, however I am more than happy to pay a premium to have this done for me.I still want to focus on investing in properties in CT, mostly New Haven, Bridgeport, Milford, West Haven, and surrounding areas.

JustineGreat job so farYou have a lot of skin in the game and more risk.

My future career is in real estate and my goal is to not have to get a job after college, instead working for myself(hopefully with my dad) as a real estate investor/developer.

He's an agent in town and does a great job for many of my clients.

Nice job adding that into the math. 3.