This is very possible, Abyr. This is what modding is all about.
It will be very easy for you to replicate a tavern or whatever room you want in Oblivion's TESCS because all the buildings come pre-made now. Not like in Morrowind TESCS where we peiced most of them together.
As for scripting, I'm pretty sure that you can script the NPCs to walk to certain places, sit somewhere, etc. If not, you could have things set up in TESCS and then go into the game and walk each player character through the routine you want him/her to do and then splice everything together I guess.
I'm not so good a scripting, but I've done alot of building for Morrowind. Oblivion's construction set is very similar. To get you started and learning what to do, the best thing is to find the thread we've already started concerning learning to mod.
Here