Based on my research, in Pittsburgh, the school board tracks sales of homes and if there is a significant discrepancy between sales price/current assessment values, they will appeal and you get a higher tax bill.

Research the operator's track record and read the offering documents.Like Evan said, a syndication = pooling of capital, regardless of the asset class or the part of the capital stack the investment is applied to. 

Or only invest what you happy to walk away from if your taking a flyer with someone starting out with no real track record.

He offered the course on 8-Track...well, I suspect he did. 

With the booking history, the lender will just be looking to see if you are on track to meet the AirDNA projected revenue for the year. 

In this day and age, not having a online Prescence and clearly documented track record is just a huge red flag

You should still get a mortgage statement, I don't see anything major you need to track here (missing your entire context please keep this in mind).

The faster track on rentals  (cash-flow wise) is to do short term rentals like AirBnB, etc….

Just open a separate bank account, give it a business name and keep track of all income and expenses.

Dual agency is an abomination before the Lord.