Hey, I just started leveling up a new character... It's going to be a mage, and I'm wondering if I do the College of Winterhold quests really early in level, will I end up getting crappy gear from it as opposed to waiting until my 40s to do the quests?

If you are referring to the Arch Mage robes. I don't think they scale.

Depends. I think some quest rewards (the Mage's Circlet is one example) are scaled, but some, such as


are not. So it depends. Bear in mind your enchanting should be able to compete with any found enchantment if you concentrate on it by the 40's.