Many people do it their first time but you need all your ducks in a row so it goes smoothly

For example there are a few states like NC that the NC Bar as of April this year no longer allows attorneys to double close UNLESS the buyer in the first transaction funds the deal with their own funds or a transactional lender.Then there are states that no one questions it and things go smoothly using "pass through funding" utilizing the end buyers funds to pay for the first transaction. 

Step 8: Execute a smooth and timely Closing by avoiding unexpected closing costs. 

I have been holding a SFR in Philly for 6 years and it has gone very smoothly. 

. - THE CURRENT DILEMMA: Now involved in text convos - I told the tenant that I will personally come to the building on Monday to see things and smooth things over with him.

The perks of doing it locally is that you can be on site as needed and make sure its all going smoothly. 

If so, make sure you are able to get to the property every so often to make sure it is running smoothly or have someone there do it for you.Also, have you thought about keeping your old residence and using it as a rental?

That worked smoothly, however, after expenses I ended up with $89,000 ("boot") in cash in my pocket.   

You can probably get another 10 years+ out of it at your current usage, assuming you're running it regularly to keep it running smoothly.

It's going to take awhile to get the right price for good quality work but I think it's worth it.Other than that, hope everything goes smoothly!