A bandit ringleader (a "named", i.e. a boss of that dungeon, cave, etc.) were the only ones that carried enchanted gear (like + 5 str). It's true that they did all carry Daedric or Glass, eventually. The game just needed more armor variety, that's all. As for enemy leveling, I think Oblivion engine had the means to make it right, but the developers didn't have the time. For example, there were some characters that did not change level. A few of the guards, at least. Now, this could have been used more extensively with more enemies... in combination with the auto-leveling of the other enemies, which was + or - 5 of your level (or something similar). I agree with the system to some extent -> because the caves, dungeons, etc. regenerate enemies at a later time. Also it's nice that, now that you aren't level 2 anymore, neither are they. Who wants to go raid a dungeon only to find out everything in there is weak as hell and the items: worthless. They wanted you to be able to have a challenge in that dungeon, no matter when you decided to go there. Because they spent a lot of time and work crafting the dungeons, puzzles, and traps.