When I play, I don't play to be "the best character possible as soon as possible", and I always tend to make choices that make me weaker overall in the game. Like in my Nord warrior game I'm playing - I refuse to wear anything better than basic steel, and mostly because I like the way that armor looks on me compared to the others. I may wear ebony or deadric when I get it (I haven't seen what they look like yet), but it really depends on what it looks like on me and whether or not I'm satisfied with that look. I did this in New Vegas, too. I wore some modded armor that I downloaded that was not that good at all when compared to just leather armor. I enjoyed the game more because I thought I looked cool and it always made the game more difficult because it was easy for me to get killed.
Anyway, I feel that's how everyone should play this game - make conscious sacrifices for the enjoyment of the game for the sake of filling the role of the type of character you want. I just want to look and be like any other person in the game - just a regular shmoe - that happens to have this unique ability with shouts. I rarely see any main character wearing something that looks out of this world like deadric or dragon armor, but then again I'm not that high level yet (highest is 29, but I started a new character). You're really missing the point of the TES series if you're trying your damndest to rock out with the best gear as early as possible.
I will, however, admit that there does seem to be some discrepancies. Rarely is a game right from the get-go. There will undoubtedly be patches by Bethesda, and eventually mods that increase the enjoyment you get out of the game.