@Brad Hunter no plan really just hold forever, raise rents at each turn.

@Steve Hall I guess I did leave out the fact that the reason these properties are cash flowing lower is because I'm factoring in cost for a property management company.

These type of lenders have their products designed for RE-investors, so you see things like higher leverage and shorter seasoning and your personal income is not factored into the underwriting, which typically is a HUGE deal for RE-investors. 

What are some factors that are playing in my favor?

Also factor in what a vacancy will cost you. 

It appears that the income is the most determining factor. 

Im sure there are points and fees to be charged for the loan upfront which you would want to factor in.

Hey Will - we are based in South Florid (Boca Raton, Delray Beach area) and we are seeing some success with converting long term rentals to Airbnb short term rentals due to probably the same factors as you - close proximity to the beach, A/B neighborhoods, etc.We were hesitant to use one of these high cost Airbnb management companies as well, as they really dig into your cash flow.

Also factor in the location/condition of the property.

Private lenders, Hard Money Lenders, a "subject to", an Lease Option, or a Private Lender don't usually care how you do the ownership. but most of those require some cash in the deal or "sweat equity" as a safety factor for them.