IMHO you should tell your friend to go ahead and buy the box set and all the live sessions. He is going to end up there anyway! hahaha They are all excellent.
That's what I did anyway. Bought a few singles. Then, I bought the box. Then I realized it did not include the live stuff. Ended up with all of those as well. Dexter is great in all of the periods. The Steeplechase stuff is some of my favorite along with some of the late Columbia dates with Woody.
Enjoy the journey!!