I would recommending looking at your property through the eyes of the NBA, or Next Best Alternative, to see if there is a market for you property as a mid-term rental. 

Are there any red flags I should watch out for when dealing with buyers who propose alternative arrangements like this?

With time management, sourcing materials and learning how to complete task on your own.

However, as W2 earners, these losses are considered passive and can only offset passive income unless you or your spouse qualify as a Real Estate Professional (REPS) by meeting the 750-hour and material participation requirements or STR is used.

(I realize there are alternate structures - this is how we are doing it.).

Its return is achieved due to an alternate rent model.  

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Alternatively, you can look into filing an affidavit.For the court hearing, be prepared to have all dates and proof to show the judge non-payment and any dates/times you interacted with the tenant.

To me the cost of purchasing cash flow is too high, better off being cash negative 2) alternate rent models: mtr, str, rent by room.  

Compare these with potential financing alternatives, like a DSCR loan or other commercial products.Exit Strategy: What’s your long-term plan—hold for cash flow, refinance, or sell?