I heartily agree with everyone who said
"MSF course first!" As to the choice in first motorcycles, it is hard for a 50 year veteran of two-wheels to reflect on his experience...they don't sell Cushmans any more. I tend to agree with those that say a little dirt riding experience can't be beat, as far as developing skills goes. I also feel strongly that most riders start out on motorcycles far too large and too powerful these days...and that includes the Spyder. I'd recommend one of the smaller dual-sport machines, say 400 cc. Sufficient to get around in traffic, lightweight and maneuverable, and you can get them off onto dirt roads and trails to further develop your skills without the added distractions of traffic. From there on, with a couple of years of experience under his belt, he will probably decide for himself which direction he wants to take.
-Scotty