I actually LIKE stumbling into a barrow and struggling to get through it only to find out later that it was for chracters 5 levels over me. WOOT... how kickbutt am I for making it?
Indeed. And this is, IMO, more fun that knowing that largely every cave is just right for your level and will contain a reward chest somewhere inside that is just right for your level. Also, if you do this or that epic quest then the enemies will be just right for your level and the reward will fit your level. Which means it will be garbage 15 level-ups from now. That's just not all that fun and it doesn't make much sense either.
What I'd like to see is discretely leveled enemies combined with a good number of set enemies and of course no leveled items ever. It's okay that more generic enemies such as bandits or trolls or various deviant mages get stronger as I gain levels, as long as it's not taken to ridiculous extremes. It's insane to have bandits in glass armor but having both a level 10 and a level 20 base version of a common bandit, with largely the same equipment except maybe grindstone / workbench improved, and the skills and perks you'd expect from a level 20 bandit. Rather than going beyond that sort of scaling, I'd prefer to see raw numbers of bandits increase. If you're level 60 rather than 20 then instead of one bandit leader and three bandits, there's now two leaders, five bandits, a couple of marauders, and maybe a master bandit.
The advantage here is that instead of a few stupidly strong enemies that make absolutely no damn sense, you still get a difficult fight but at least it's kind of epic. One on one you'd crush them easily, but it's not a one on one battle. This approach is tried and trusted and it worked brilliantly in the IE games. Take BG2, for instance. At low levels you'd meet a mummy or a fledgling vampire or a gauth. At high levels you'd meed a horde of zombies lead by a drowned dead (or maybe just a lich), an older vampire with a posse, or an elder orb with a few beholder friends tagging along. What would be an iron golem at low levels would be an adamantite golem at high levels. This kept the game somewhat challenging regardless of the order you decided to do things in, at least for the average player.
Of course, it has to be said that static enemies combined with the odd bit of Skyrim level design that blocks you from retreating is not the best idea.