I'm not worried about finding the next deal or anything and as far as management goes, Florida doesn't require any license for self managing.

As far as living a life of financial freedom with one rental- that is unlikely to happen.

Hello Ilya,Where are you looking at purchasing your 1st property.When converting a property from a single family to a multi family, you will need to check on the zoning requirements, depending on your location, not every location has zoning.As far as lending goes, it is far easier to finance a single family up to a quadplex, than financing 5 plus units, the DSCR Market for 5+ units is extremely low right now, and there are few if any lenders in that space.For financing 1-4 units, there are Millions of dollars chasing those loans, so you can easily obtain long term financing, at rates between 5-7%.Please reach out if you have a property identified, and I can help you with financing options.

What are my options as far as securing that second mortgage and what would you recommend, Conventional, FHA, Hard Money?

The cashflow over the long term is by far a myth when you buy right and budget correctly. 

It is so limited and seems like you have to login to the full site for most tasks especially when leasing and trying to get to Tenant Turner to see appointments on our iPhones.We are considering changing platforms and my current software spend with Tenant Turner is roughly $100/month or $6.67/unit.

As far as what your girlfriend's thoughts are, well that just depends on what kind of a relationship you are wanting to have with her and how serious it is now.

Each deal is so different that its tough to tweak the proformas i do have. 

Each state is so different when it comes to the laws and even the bidding process.

As far as plugging in numbers and ensuring you're doing so correctly I recommend using the calculators on BP as a starting point.