I recently just paid my mortgage for the first time and had to come out of pocket for her portion of the rent,     Before you get into many more deals make sure you have reserve funds set aside as though this does not cause you stress, its a business deal.  

I would just buy a multi-unit property.Having 4-5 different properties could be a headache, also multiple closing costs etc..Just buy one commercial unit, live in one, rent others, and even if you don't rent one of them at some point don't get stressed out.

@Craig Jackson I've been in a similar situation that you are currently in and it can be very stressful.

You can still make money from no equity but (to me) it's more stressful and you never know what's going to happen, so it's very difficult to plan ahead.

I have the desire to become more, to be more, and to reach a point of my life where I can enjoy my family without the stress of my current source of income. 

Being debt free may also make the jump into RE investing a bit less stressful.  

I recently bought a duplex that was a week from auction and it was stressful for the seller,us, and the title company to get everything lined out and closed.

Living in the same duplex or 4-family building as your tenants can be very stressful at times.  

I cannot stress enough that you are the one taking all the risk here.

It's just more stress than I can handle.