I want to know how much I could afford for the second house, because that will determine how much I actually spend on the personal residence property.  

I am 19 years old and I can afford a little more risk as I obviously have some time before I am going to retire.

Due to how expensive it is here, I am open to pretty much anywhere in Florida that I can afford and makes sense financially.

My bigger concern is whether she can actually afford the rent long-term, or if any "unexpected" event from here on out will put her further behind.

It depends on how you measure "deals are better"  Some of the measures access to entertainment & access to business corridors which results in low vacancy rates.

What advice can you give a newbie like myself that just wants access to quick, affordable, reliable information?

Hello, so I have been interested in real estate for some time now and always wanted to get into it as I love property and would like to help others get affordable housing at the same time the cash flow opportunities attracts me. 

I would get the lender first so you know what you can afford and then determine how much of that you want to spend.

I am having the toughest time finding a reliable and affordable contractor.

I found this property on zillow and was not too successful at negotiating the cost in my favor because although the seller was motivated because he was going through a divorce he could not afford to go any lower.