To my mind, the randomization of encounters outside of towns is a huge improvement and while I really liked the schedules Oblivion's people have, I always felt pity once I reached around levels 10-15, because then it was not a given any more that the Skooma-dealing Khajiit reached their destinations. As a sidenote, I used to play Oblivion a lot on PS3 with the GOTY-edition, kind of vanilla compared to the over-modded monster that is installed on my PC, and I found it perfectly viable for the PlayerCharacter, not the free-roaming NPC.
The dragon's advantage over the Oblivion-gates is merely that you can dispose of them faster, even when ghosting the gates in order to close them quickly. My game seems to feel pity with me, because dragons don't spawn on every corner, I'd estimate the time between the encounters to be roughly two hours, which is fine for me.
The cities are very different, and I can't really tell, which one's I like more. Time will tell, I guess... I really hope that the houses I did not enter yet have some kind of secret to them. From what I saw just yet, I'm not going to be disappointed beyond belief. The inhabitants are completely new to me, as are the political struggles dividing even single towns. I have not yet made up my mind which side of the coin shines brighter, though I heard NPCs advertising their opposition to be the true side. Investigations pending, later.
Taking into account that magic isn't really favoured by and suspicious to the Nords, I think it was necessary to be reflected by the abundance of local outlets of a mages guild. The court-magician leads a kind of secluded life doing his thing and doesn't disturb the majority of people, so I - as a mage - have someone I can address, and as an étudiant d'art I kind of understand that I am not always greeted with greatest respect. Though I understand that character-interaction needs a lot more fine-tuning by the developers in order to reflect the improvement we make while progressing with our studies.
All in all, I have to say that I am not disappointed by Skyrim at all. There are many, many locations I still need to enter for the very first time and given the fact that the next installment of the Elder Scrolls will take time to materialize, I am in no hurry. Even the things that feels strange at the moment just take time to be familiarized with.

Come on people, really take a minute to look and compare the two...