I know this question is highly dependent on the individual and personal circumstances and preferences, but I would love to hear what route everyone would choose in this scenario.  

I know I have been doing it for decades.. and I can count on one hand how  many have made over 100k.. although I did one that I made 750k and that was a once in a lifetime.. and had a lot of extenuating circumstances on it..

I kept in contact with this seller just for the simple fact that circumstances could change and oh boy did they?

@John George you made some mistakes so the tenant has been "trained" to call you and whine.Do not respond to the tenant under any circumstances.

Most folks feel comfortable at a holding period of more than a year but there could always be unique circumstances that would change the appropriate holding period. 

What path you take depends on your personal circumstances, investment style and personality type. 

@Angela Meraklis-LyonsI'm so sorry to hear about your unfortunate circumstances.

But it is possible under the right circumstances.  

If he discovers unforeseen issues and the deal falls through, he’ll be happy his time is paid for and will be happy to work with you on the next project.

Give them the requirements up front and let them know the fee will not be refunded, under any circumstances.