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.

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.

Will make sure HOA is ok with it#2 I ran numbers today and I'd be the same at 3k/mo as I would long term'ing it (paying our friends $300/mo to manage (and upwards from there as the price increases above $3k), but would still need to buy furniture in addition.

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.

If I could make it cashflow, that would be great however back to my original statement, I am just looking for a way to afford a getaway spot for several days a week. 

If they want to do affordable housing in larger cities (eg Toronto or Vancouver), it could work in select markets.