What are some factors that are playing in my favor?

Also factor in what a vacancy will cost you. 

Vertically integrated  they have call centers they have closers that run out to the property the second they get a lead they have office staff to handle the transactions..  3. owner is sharp knows the business inside out.. and frankly would do very well at just about any business they wanted to work in.those that do this on their own with zero help.. those come and go with the wind.. failure rate I suspect is far more than 90%Along with Markets matter.. do you live and work in a market with excess inventory that can be had.. or are U in a very tight market.. tight markets are tough..

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. 

They are in a market where you have a very limited amount sellers you have to be able to compute multiple factors per transaction and you have to spend money on marketing. 

It isn’t near profitable when factoring in the mortgage and taxes and such.