I wouldn't dream of such an arrangement in a city or any other location where there's a myriad of choices, that costs a whole lot more than a couple hours' headache every several months.  

Because of short term rental most closely resembles a motel or hotel.

To qualify for a conventional loan, your second home must:Be a one-unit property that’s available and suitable for year-round use.Be occupied by you, as the borrower, for some portion of the year.Be controlled exclusively by you and not a property management company.Not be a rental property or timeshare arrangement.

You could lock in the same payments as a seller finance arrangement with at least some probability the buyer wouldn’t actually end up buying, and you could collect an option fee from them.

Another thing you could consider is asking the bank if they could cross collateralize the downpayment on your new deal with the equity in the other properties - basically you would put the equity in those up as the down payment (or portion thereof).If you are in a value add situation, maybe you could use hard money to help fund the deal, or downpayment, and then refinance to a more traditional lending arrangement down the road once you have increased the property's value?

If you're not comfortable visiting the jail, you may be able to arrange a phone call or video chat.3.

I'm grateful that she sent it my way, but I would have liked to know about the arrangement ahead of time.Thank you for any insight you can give me.

They wouldn't have to make decisions over and over about whether or not they want to fund your next property.This is the same setup I'm arranging with my banker. 

PM me and we can arrange a time to chat and see if it may be a good fit.  

Let me know if you'd be interested in chatting with us and I can arrange a phone call or even a meeting if you happen to be in the area.