Contrary to what BOX MAAAN posted, I actually liked the equipment degradation in Morrowind. Repair tools only lasted 15-15 uses, which was awkwardly low, but it worked passably well in spite of that. In Oblivion, the wear effect was far too rapid, and at low to medium skill the repair tools broke almost immediately, so you had to carry dozens. That was just annoying.
Playing a Bosmer seemed like a good idea in Morrowind, until he took a couple of hits. The horrible and annoying squeeking and moaning noises coming from the character quickly convinced me that it was a very bad idea, and I've never played a Bosmer since.
For whatever reason, my PC doesn't seem to handle DOSBOX well, so I've never been able to properly play Daggerfall on my system. I had dabbled with it on a friends PC years before, and it seemed to function well enough then, but neither the configurable nor the pre-configured versions will consistently activate the weapon on my own system. The controls seem to be really awkward for movement, too. Worse, my character just stands there and takes hit after hit while I click and drag the mouse back and forth or side to side repeatedly, trying to attack. Every 10-20 mouse swipes, it will work and the character will actually take a swing, then stand there again. The game is essentially unplayable for me.
As for Oblivion guilds, yes, you get quests, but they don't feel like "guild work", they feel like a "storyline". In Morrowind, I went to guilds in order to get work. In Oblivion, I wanted "work" and got a "questline" instead. I understand that its even more that way in Skyrim, except for the radiant quests, which SHOULD be at the start for generic "work", instead of after you've already finished the questline and become head of the organization.