I admit I was only half listening because my volume was turned down so low but I thought Michael knew him from law school (maybe they're both alumni who graduated different years?).
Michael mentioned that supposedly Gloria never liked Craig so I'm assuming that Michael and Craig know each other for a number of years.
It would be nice if we see Craig more frequently because he is indeed quite nice looking! And that connection I mentioned might add a nice twist for both characters.
Neil is Devon's father. Guiding and paying for college is what father's do.
Neil never helped devon set up any business. Stop with the fan fiction. Neil wanted Devon to follow in his foot steps and go into business. Devon went into music against Neil's wishes. Devon worked for Tucker then Kay. Then set up his own record company with an investment from Abby. Then he went to work for Neil at Jabot for about 6 months. Then got his inheritance and stilled worked for Jabot until Jack fired him.
Either way, Neil is still devon's father dishing out advice. Which was the only thing he's done for Devon since Devon became an adult.
I don't think there is anything wrong with gallows humor. I've had at least one uncontrollable laughing fit since Trump was elected. People cope in different ways. I know it's hard. I'm going to hide in fiction until Monday.