They have more skin in the game then you do.Make sure you get clear title.

I would be remiss if I didn't plug the benefits of a PM (and I am a PM and the Orlando market is the only market we service) by only taking out 15% of revenue especially when what should happen is an attempt to "find" the 15% fee with amazing bookings and really using dynamic pricing to get the best ROI for your unit.  

Then another factor would be dynamic pricing - if the rental company or self management owner has implemented a software to always be competitively priced in our market.

Yes it is "possible" to get a deal partnering with someone else, but no offense when you have no experience, no history, and no skin in the game (financial contributions to a deal), I doubt anyone would want to work with you.

I'm also wondering whether it is too risky (i.e. introducing this into the family dynamics). - If we do go the way of transferring the property from them to me, is there an easier way to do things than a sale?

It brings tourists into what used to be residential neighborhoods and really messes up the dynamics of the neigbhorhood (I see this in my own neighborhood, which has tons of airbnbs).

By using dynamic pricing and the correct revenue management strategy, the homes will definitely cash flow and perform very well.

That makes sense but there is more than one way to skin a cat so to speak.

No.From a lenders perspective typically they want to see you put money down, otherwise you aren't putting any skin in the game. 

As a lender, we wouldn't touch a deal where the investor does not have skin in the game.