Lots of locals trying to change that for the better but it is tough.

It's tough work but put pencil to paper and make an honest assessment of how much damage you could handle.

to leave current job, secure financial freedom faster, bragging rights, prove something to ourselves or even others. 

I have some money saved and would like to put that for downpayment and reviewing previous post I assume that getting a loan (mortgage) for a Series LLC will be even more difficult that for a regular LLC (which apparently is already tough).

Tough tenants, almost impossible to find a good PM.If you're interested in CT, consider New Britain, Manchester, Bridgeport, Middletown, New Haven.

Self managing can be tough depending on how many properties you have in your portfolio and how much time you have to dedicate to it.

Especially if they are in a tough situation, your inexperience could lead to making their situation worse. 

The 3/4 tenants could prove to be an issue 8.

Your answer as well as the others just proves there are no dumb questions. 

That's a tough one since lenders traditionally want proof that self-employment income is stable, consistent, reliable, etc.