If I take 3 characters through these games which ones should I take? I plan to take an imperial thief who uses a lot of speachcraft and enchant/alchemy as spells... a High elf pure mage.... and an orc warlord! So which should go where or doesn't it really matter? For instance I know morrowind vanilla goes well with any archetype, but would the others suit any of these: stealth, combat, magic moreso?
Doesn't matter. If you can survive as mage at Red Mountain, then Mournhold and Solstheim wouldn't be a problem. It's not gonna be different in Tribunal and Bloodmoon, not in gameplay that is. There are new enemies, like spriggans, durzog's and so on. But the mechanics remains the same. You don't have to create a chacter for each game. It's actually so that you just continue with your existing character through both expansions. That's the setup.
That's true, but I think Claudius's imperial thief might have a tougher time surviving than his mage and warlord. There are certainly things to do as a stealthy character in both expansions (mostly in Tribunal though), but they are more focused on telling their main stories and they are very combat oriented - and that might pose a more serious challenge for a thief, but makes it more interesting too. I did play a stealthy bosmer through Morrowind and it's expansions and it's far from impossible (especially with good use of the bow and a high skill in that weapon use).
Call me a purist, but I always felt best playing the vanilla and Tribunal main quests as a Dunmer, and Bloodmoon as a Nord. Otherwise, I generally feel like I stick out a little bit too much.
I get what you're saying - when I had character that was Nord and Nerevarine it did feel a bit off. On the other hand I don't really think one should think of Morrowind, Skyrim or Solstheim or any other region in Tamriel as being exclusive to all others than the traditionally dominant race. At least since the empire conquered all of Tamriel mobility seems to be extremely high - consider the many imperial citizens who are colonizing Vardenfell in Morrowind. On Solstheim there's a legion fort and the east empire company is in the midst of establishing a mining colony - so if you're there what ever your character's race it's perfectly in tune with the whole idea of the spreading of imperial interests, culture, civilization and commercialization.
