Any advice and book recommendations are welcomed. 

Regardless of legal nuances, I can tell you from extensive professional experience: Don will WIN an IRS audit for his Subject-to interest, as long as he can show that he made the payments.

This is great advice!

Quote from @Kory Sheldahl: Hi everyone,I'm seeking some advice regarding a property I own in Hawaii that is currently rented to a military tenant.

But for the best local advice, make local connections in the market with Host groups and Rental Associations.

But either way, we didn't trust him as a renter and we moved on.Thanks for the advice! 

As a cross-border investor, I'm likely going to need advice on entity structure to protect my liability while also not being double-taxed, I'm going to need to network with experienced investors/property managers/agents in the Cleveland area.

One key piece of advice that I would give anyone looking to turn their property into a rental would be to make sure you are in a financial situation to do so.

Yet, what positive advice have any of them really given to help you?

If you have a perfect closing and first 3 months your dreaming Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?