1)Do you think it can be done?
Certainly. We already have randomized quests in Skyrim. Skyrim also introduced a new feature called Dummy Objects. Dummy Objects are hand-placed items in the world, as in Morrowind, but they are also leveled. So, for instance, a hand-placed Iron Dagger on a table may be Steel or Orcish at higher levels. If they can level hand-placed items then I don't see why they couldn't randomize hand-placed items as well.
Martigen's Monster Mod for Oblivion randomizes stats of enemies (skills and attributes, size, confidence, aggression, disposition). Every time you load a save these things are randomized from scratch. You never know what you will encounter when you meet an enemy, even with the same save. So we know that randomizing Disposition can be done.
2)Should it be done?
I like the randomization that Mart's mod brings to Oblivion. It makes every encounter feel new and exciting. But beyond that, I think there is room for a judicious use of randomization.
3)If yes, do you have any concerns regarding the concept's implementation all the same?
I am not enthused about randomizing hand-placed items. I think a little of that will go a long way with me. I have no problems whatsoever using player knowledge. After years of role playing, it's second nature to me. The way I see it, permanent hand-placed items help to make a game world feel real, stable, persistent. I like fixed hand-placed items for the same reason I like fixed hand-made landscape: they both help create the illusion of a permanent place, a real place. When things change too much a game world stops feeling "real" to me.
I also think randomization of non-hostile NPCs would need to be strictly controlled. Some NPCs are always going be friendly toward the player: it's the nature of the NPC, or of the situation they are both in. I wouldn't mind a little variation her and there when it is appropriate, but I think randomization of Disposition would need to be applied with nuance.
Myself, I would rather see race, class, and past deeds have a big effect on Disposition in future games. I would add a bit of randomization here and there as flavor when it made sense to do so.