They have to have an established contract with the bureaus in order to report.

I realize we’d probably want to bring in a real estate attorney, but I’m assuming there are models in place that are probably well-established for such a partnership that I know nothing about.

Eliminate debt, establish a budget, and save.

If you want to establish a long term relationship with someone who lives eats and sleeps creative financing and loan products - I recommend getting in touch with a well-versed broker who manage the relationship and introduce you to competitive products in the market.

Also, in regards to a per diem, I'd like to be a bit more optimistic that I can establish the right checks and balances to ensure that the contractor is not skipping corners.

Seacoast NH, for example, has some great potential with short-term rental markets (Airbnb, VRBO), especially in towns like Portsmouth or Hampton, but the regulations can be a bit tricky.

From my experience: SMS has the best conversion but is the most regulated, so it depends on the rules in your market. 

But before that you need to establish that you purchased it with an investment intent. 

However, the market is competitive, and rental regulations are becoming stricter.

If it’s verbal, they’ll need to document any prior communication or payment records to establish the relationship.If the PM is completely unresponsive, they may want to send a formal written demand for communication and payments via certified mail.