If your brother wants to try a get every last mile out of the tranny, then I would go mild. Sounds like he does not even need the 300 hp. My 97 is pretty much stock (plate moved a little forward), and it pulls my 6500 lb 5th wheel well. It ain't gonna win any races when empty, but will keep up with the big block chevys when towing. I'm trying to get every last mile out my tranny, when it goes, then I'll do the DTT or ATS thing. Once thats in place, then it's bomb big time.
I would start with a complete flush and filter change of the tranny, consider supplimental cooling of the tranny, and maybe check out the tranny pressures at all the ports per DTT's website (they have pretty good instructions on how to). The pressure readings will tell you the state the tranny is in, and MAYBE you can up the pressure A LITTLE BIT. Of course, all of the usual checks like overflow valve, fuel lines, filters, linkage, etc. Make sure everything is right before going on.
As far as bombing goes, (just my opinion) a #11 plate, free flowing exhaust (5" with or without muffler), boost elbow, free flowing air cleaner (BHAF), would be a nice addition to the way the truck runs without going crazy. When the tranny goes, get a good one, then the sky is the limit. When the tranny is upgraded, the only thing he will have to redo is the plate, and no problems trading in or selling a number 11. Then go with a new plate, turbo, bigger injectors, manifold, etc. I did not mention injectors in initial bombing cause they can get pricey and for a stock tranny, it's not worth it to change them, just to go bigger later when the tranny can hold more power (bigger injectors).
Hope this helps a little, Kevin