Shannon, I was worried about how Ricky would be during our first winter with him. He was much younger though, 4-7 mths., but he didn't mind it one bit and when there was snow, he actually did the RLH's out there regularly.
What I do now, is put a suit/coat on both of them (because the size of the snowballs stuck to their hair create mats and large ponds in our house!) and they go nuts out there. Cold or no cold. I limit them to the deck, otherwise we'd have to shovel out half the yard and that just ain't gonna happen. lol
It's one thing not liking the cold, but once there's snow on the ground, I'll bet that MoJo will have a blast and you won't be able to call him in!
Until then, maybe you can try using booties on him which may help.
As to the grooming, I've been keeping Ricky's hair quite short for over a year now simply because his hair is very thick and slightly cottony on half his body. It is a huge ordeal to comb through it and I make sure it's done thoroughly. Better for him and for me to keep him short. Sammy's hair is silky and easy to comb, so he's got a longer coat. Do whatever suits your lifestyle, Shannon. If it makes life easier to keep his hair short, then go for it.