I'm still not following what you're saying about where the list service obtains the "current market value" of the home.

Not sure what market your in but if you can find something that you can potentially at the very least break even then that's a win in this market.

There is a lot of uncertainty in the market for institutional capital, which funds a lot of these types of loans. 

With savings rates so high I'd save in a money market mutual fund until I had enough to get rid of PMI on my primary.

The offers I'm getting are off market offers through a broker.

Off-market property, which is likely the case if you were buying from a wholesaler, has no financing or appraisal contingencies most of the time.  

I am not a lender but I work with a lot of buyers who utilize second home loans and I am 99% sure you cannot buy multiple second home's in the same market. 

If you look at Orlando, 365 market for the most part but it is one of the toughest markets to succeed in.

Based on your financing options, you are going to be limited to 4 units or under, given 5 and over become commercial lending, so no FHA or owner-occupied options.I am assuming you plan on living in one of the units, but to be clear, that will be a requirement for at least 12 months, under most mortgages.You may get other's posting about talking with wholesalers or trying to find off market deals.  

I've been looking at markets across the US and Florida seemed great for us.