If you let the tenant know that you will handle the matter fairly and honestly, they will have nothing to fear.For the future.... it's best to do periodic inspections during the tenancy and to charge for damages as they occur or as you discover them.

Keep a cash reserve in case we experience 100% vacancy in the rental for a period of time.

Well that is where the Termination "Option Period" would come in I believe.

And, I am educating myself to try to start an e-business based upon my years in RE. 

So I’m really eager to take action and put all the BP education to use.

My tax guy is great and should help me through some of these questions but I want to educate myself and not be 100 dependent on what he says.

The problem with keeping the condo in my opinion is that you are losing money every month even with a perfect tenant so any vacancy periods or a tenant whom does not pay and take months to evict would be detrimental to you and is a huge risk.Also if you have not done so already I would get term insurance on yourself because your wife would not be able to afford your home if you were to die tomorrow.

You don't need to ask him to mentor to you but just ask him your questions and see if he'd be okay with you periodically following up with him or eventually partnering on a deal or something like that. 

@Chris Pohlson get educated on commercial/mfam and financing associated with the asset class. there's more scale and the financing (debt and equity) can become easier. 

It sounds like your vacancy is a pretty short period and you will need time for makeready anyway.