.$365K mortgage at 7.5% - $2,550/MoHOA - $460/MoTaxes - $306/MoInsurance - $200/Mo?

They need the insurance declaration pages (1-2 pages showing the annual premium and the insurance agency contact info), property tax bill, and mortgage statement. 

Would it be a conventional mortgage as a 2nd home?  

If we were to buy something in Lake Nona, it would obviously not cash flow as we would have her move in and essentially just help a bit with the mortgage, but how is appreciation looking in that market? 

if you’re looking for an investment angle, you might consider moving into a multifamily house, such as a duplex, where the other tenant would probably pay for your mortgage with their rental payment each month.  

On the ground or online; I happen to be in the area this weekend. 

I have never heard of that, I cannot find anything about that online, and I have a friend that has been an agent for 20+ years that said Fannie Mae properties are always immediately listed.

The issue I run into, based on what I can put down, is that I would most likely have to split the mortgage down the middle (I pay half/Tenant pays half) based on current rental rates and current mortgage rates (considering what I can put down).

I would also point out that it's unlikely the rates will come down close to 2.99% within the next year, so sitting on the sideline for years is a risk in of itself.Alternatively, you could get a 2nd mortgage that would allow you to keep the first mortgage at 2.99%.

His primary mortgage was sold to a private lender in the early 2000s and he claims he had to give an explanation each time as to why he financed with a private lender with such poor reputation every time his credit was pulled.