HI Scott--
Benson may be able to provide statistics re your question about the oak decks, but I've been looking up build records for people for a while now, and oak trim is more commonly seen on the guide model Old Towns than on HWs. HWs of CS grade more commonly had ash or birch decks, thwarts, and seat frames. Don't know why this is... CS stands for "common sense"... so your canoe is very sensibly trimmed in oak! It may be that oak is what they were trimming all CS grade canoes with that day.
I think orange could be very pretty... really set off the wood interior and look spectacular if you're paddling in the fall where leaves are turning all colors. But the consensus regarding canoe-color is to paint it whatever suits you.
Kathy