So you get to Whiterun, and tell the Jarl about the dragon that's turned one of his towns into fried and extra crispy. He's very pleased, and seeing as how you're dressed in mage robes and hood, he rewards you with...steel armor. Steel armor? Is he trying to ridicule you because you're a mage? No; he's got a mage on staff. Is he blind? That's possible. Certainly the Companions seem to think you're a rough-and-tumble melee type. What a strange land...

My thought is that when we finally get the construction set, quest rewards in at least a few cases should be corrected to reflect the very obvious profession of the character. If they're wielding a bow in light leather, they're probably not a bruiser, nor is someone in robes. Checks on weapons and armor should make that clear. We can't affect spoken dialog, but in the case of Whiterun's Jarl, we don't need to. He doesn't say anything about what he's providing as a reward, only that he's giving one. So the reward can be changed. That's just one example, but hopefully it will start somebody thinking along the lines of making the game keep a little more in-character on this point, and provide the player with an appropriate reward to encourage they're continuing on the path they've chosen.

I think it's reflect on your skills or random, I'm not sure.

[1] Got a shield with magic resistance when I went pure warrior.
[2] Got a 2H one time as a mage/warrior/archer
[3] Got a 1H another time as a mage/sneak.

My sneaky mage got a hide shield with +40% frost resist... I actually found it quite appropriate, since that actually is pretty handy when facing a frost dragon, and I wasn't going completely armorless, anyway.

Yet my character had chosen the path of the mage, was wearing robes, and had spells in both hands. Maybe the Jarl had his glasses off that day. Those late nights, you know.

I think it has to do with that he sits in that chair for 12 hours a day, waiting for someone new to talk to him.

Equipment checks would make more sense from a reality standpoint, but skill checks would make more sense from the standpoint of getting equipment that fits your style. I'm 99% sure there are already skill checks going on all the time in game as random NPCs remark on my mage's ability to use destruction as I pass by.

For main quest rewards, have it check your highest 3 or so skills and give an item based on those.

I've gotten:

1. A destruction staff.
2. Conjurations staff.
3. Steel armor.

All three times as pure warrior. (Yeah I had some issues) It's random.

Have you spoken to the Jarl's son? I figure the Jarl wants as much clanking and banging going on about him as possible so he doesn't have to listen to the little brat. He knows you're a powerful dragon killing mage, but unless you can cast a decade long silence spell on his boy all he asks is that you humour him when you attend in court and add a little noise to the event!

What I suspected--and what I'd hope someone will correct, when the mod tools become available.

I was given a two-handed axe, which I promptly stuck up on the plaque above my front door. It went in...sideways. I think it was because I'm playing an Orc...though I was putting points in one-handed at the time already