He can start off with one of the lower price machines and buy the software that allows him to digitize his own designs. I own 2 Brothers and I can use any software for digitizing. The most important thing is for him to decide how big he wants his embroidery area to be. One of mine does a 4x4 area and one does up to 5x7 area. He can start off for under $1,000 and that includes buying digitizing software. And he doesn't have to buy the software that is "specificaly" made for that machine.
If you want to PM me, I can give you more info.