I really hope it works out smoothly for you!

Detroit is a tough market so I don't really expect perfect tenants with smooth sailing.

will it be smooth and easy that the attorney will prepare the forms etc?

You may need to flex in the transition rather than expect everything to go smoothly. 

So, where we currently stand is that we are more than likely going to give back his half of the security deposit, and half of the first months rent ( I would be eating the cost in attempt to make a smooth transition).

If I was you, I would replace it with the smooth metal ducting or the expandable metal duct (Note: This is different than the cheaper foil accordian duct.

Curious how to do that and not get tangled up and not be able to set everything up same day with all properties and run smoothly?

I think once the hurdle of getting it setup is done then it's pretty smooth sailing. 

Revocable living trusts can play a nice role if you own a small business and want the transition to go smoothly when you pass away (e.g. a family business where the parents want certain children to take over the business).

This person is obviously a game player and you need to be prepared for her games