It depends who is going to be riding on the back of his sled, and how he likes to ride.
If his significant other is always going to be along, he might want a 2-up. If he does a bunch a large group riding, having 1 guy ride a 2-up works well especially if you gotta leave 1 sled behind and go get parts.
But the fun and flexibility of 2 separate sleds is great. I, for one, WILL NOT ride bitch!!
The extra costs of 2 sleds could be a factor too. I have a 10 year old who loves to go riding. But I rent a double when I go North, and around here when there is snow, she just rides in the fields or on back.
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