I'm having trouble communicating to the tenant when to call me for an issue.

This is always an unfortunate situation and is usually a result of a lack of communication on someone's part.

Buy and hold investing is far more tax efficient.

I suggest you don't advertise or communicate any of this info to prospective tenants until you've gotten solid legal advice.

We are fully capable of taking on a project like this but my concern is that I will do something that will communicate that I am new to the business and he will lose interest.

Quite a bit of work with "first responder" communication systems.

In either case, I would love to understand the most efficient way to structure the deal. 

You would keep making the payments.When you take a property subject-to it's important to get an authorization to release information from the borrower so you can communicate with the lender about the loan.  

Marie Poe, the property was not deeded to the buyer, there was no lease or rental stipulations, I had no idea when we filled out the sales agreement what was the right way to do it, She has stop communicating.

Anything over 20 & under 100, I will say a good PM is more efficient & economical.I got this from my previous RE business experience in the past.