As best as I can tell without knowing their specific algorithm their search placement is weighted something like this: Price>No/few rules>super liberal cancellation>Instant book>Premier host>Reviews>Other.

A deal that has $1800 for expenses is a deal that will fail.

There could be negligence on your part for failing to maintain them.

I will need to explore the 1031 route and weight it against my opinion on the market. 

Chad Littell from CoStar notes that while institutional investors adjusted their strategies early in response to rate hikes, individual investors have only recently begun scaling back.July Sales ReportAccording to CoStar’s July Commercial Repeat-Sale Indices (CCRSI), the equal-weighted U.S. composite index, tracking smaller market sales, showed only a 0.2% price increase from June, with prices down 0.7% year-over-year, marking the first annual decline since 2012.

I do commercial and there are good options but the price ranges are much higher than Single Family and the risk (i.e. in retail, ~80% of the business fail in the 1st year) could be higher. 

Or if you tried it and it failed also let me know.

Quitting your job to do real estate full-time is obviously attractive.You could listen to all of us telling you not to do it, but sometimes you just have to take a chance and make the best of it.There's a lot of successful people that didn't know they could fail and succeeded despite the odds.

Hold it close to your chest for leverage and if she chooses the eviction route or fails to adhere to the payment plan offer it one time with a shot clock. 

If your systems are failing, I would be looking at your preventative maintenance process.