I have a feeling that if you use it as a rental, your emotional attachment to it will lead to you over-maintaining it, ultimately creative a negative cash flow situation. 

It’s a buy and hold situation so I agree, that does change the situation somewhat.

However, I’ve moved into a situation where I no longer have the time to do the work myself, but still love the process.

You could also put the property into an LLC as opposed to putting his name on it as well, but you would just be back into the situation your currently in, with lesser terms when you go to refi (due to LLC).

At that point I can evaluate market conditions, time of year, situation at hand, etc and provide a reasoned lease cancellation quote for the tenant to consider.

Hurting your financial situation to help them out has its limits. 

But these seem like big "Ifs".Does this situation make sense to move forward on??

What to pick comes down to your individual situation.

As for starting out with no money, a lot of folks in similar situation start out as whole-sellers.

That's a difficult question to answer without understanding your current financial situation and risk tolerance.