This property is going to be a money pit for a while, but long game will most likely show a profit or at least not a loss.  

That way if they cause a loss, their insurance covers your deductible. 

For example, you may have suspended losses or some other circumstances that change the game.

Same as if it was bank-financed.However, make sure that you can in fact reduce your taxes by rental losses.

Good Question, I would imagine the lender will want to recover whatever percentage that home represents in the single mortgage. 

A few things I do personally for clients is: create a P&L, market to my buyers list, pre-market the property online where the target audience is, and make a plan for bookings and the booking calendar to minimize losses while up for sale and operating simultaneously.  

By the time we paid the legal fees to our lawyer to do the conversion and the reduction in the balance of the loan took a major loss. 

Book losses through bonus depreciation.4.

I have been contacted by a company wanting to lease my single family furnished rental on a long term lease for men recovering from addiction.

You can also use bonus depreciation on the entire property, but only the STR-related losses can offset your W-2 income.