After spelunking through all of the lovingly hand-crafted dungeons, I'd probably look down on any randomly generated ones. The idea of being able to simply embark on a journey to a dungeon whenever I want with the promise of training skills and gaining loot doesn't exactly appeal to me: it sounds like something instanced you'd find in an MMORPG or Diablo. Everything in the Elder Scrolls world should have some permanence to it - it shouldn't be as simple as saying "I want some loot, instead of exploring for dungeons or searching through peoples' homes I'll just press this button and be instantaneously transported to a new area guaranteed to have stuff for me."
thats a great point. i guess its all based on opinion, what you say makes sense, but in a long term, say 500+ hours, youve had probably enough time to explore every dungeon, and do pretty much everything, this is a way (although perhaps not the best) to keep things a little fresh. heck, they could even make it to where most of the time there is no reward at the end, just a bunch of enemies and wasted supplys