I have such happy memories of Vivec, Ald'ruhn, the Imperial City and so forth, where I would find so many interesting places to wander and people all over the place selling different kinds of things.
Shops are needed for practical reasons of course: there's always loot to offload, and it's useful to go shopping for equipment to help with quests. But for me they serve a more important purpose, which is making the world seem like people actually live in it. Who could forget Jobasha's Rare Books store from Morrowind, or the Mystic Emporium in Oblivion? Such shops were a huge part of what made their towns seem big and full of life.
So then I come to a town (I can't really use the word 'city') in Skyrim.. any of the towns I've visited so far, anyway.. and, gosh, it looks very pretty. At a glance some of these places look just amazing. But then I try to go shopping, and there's pretty much guaranteed to be something like: one smithy/weapon shop, an alchemy shop, and a general trader shop. Their interiors and exteriors are very similar from one town to the next. There's nothing about them that sticks in my mind. I couldn't tell you the name of any of the shopkeepers. The settlement begins to feel small, no matter how majestic some of its buildings may be.
The problem must surely be the dialogue. If everything that every character (shopkeeper or otherwise) says has to be voice acted, then dialogue has a price and there will be much less of it. If you're Morrowind and you can have as much dialogue as you want without the hassle of voice acting, then you can be full to the brim with interesting characters who have endless interesting things to say. Or you can impose the crippling limitations of full spoken dialogue on yourself, and suffer the consequences.
I'm not sure if I'm trying to make a point, really. Going back to text-only dialogue wouldn't be accepted in this day and age, so there's no use campaigning for it. But wouldn't it be nice to transform the lonely, deserted Skyrim into something that feels alive?