So recently I've tried roleplaying a Pilgrim/Paladin character in Skyrim who specializes in healing, a blessed two handed war-mace, and fighting the undead. But I'm finding a lot of the content in Skyrim lacking for my kind of character - you can't join the vigilant of stendarr and there aren't really many quests that allow me to further act out as my character.

I haven't played Oblivion for a few years and I never played any of the DLC. And I was wondering would I have an easier time playing my character in Oblivion? Also, does KOTN add good content for this type of character?

Thanks

My answer would be, "Yes." . It's my opinion that, overall, it is easier to play a good character in Oblivion than almost any of the other games in the series. In fact I have never been able to play any kind of "bad" or "evil" character in Oblivion.

KotN is very much geared toward a "good" character. So it's my opinion that you would be very happy playing Oblivion and KotN.

For a pilgrim KOTN is ideal, I highly recommend this. You start as a pilgrim, you finish as a crusader. Obviously a bit more to it than that, but it is very much ideal for the honorary characters.

The other DLC's have their uses, safehouses you don't have to buy (but still upgrade) mostly. A fort ideal for the fighters, a wizard's tower ideal for mages and the apothecary, a lair ideal for the evil characters, a den for the thieves, a powerful machine that can grant magical spell boosts for anybody, then there's also quite a large dungeon to conquer and shivering isles adds a whole new world to explore.

If you're looking to play that kind of character, I'd recommend Morrowind instead. There's an Imperial Cult quest line, a Morrowind Temple quest line, and an Imperial Legion quest line which would all probably fit your character. Also, KotN is about following in the footsteps of Pelinial. While the quests makes this seem like a noble endeavour, you should know http://www.imperial-library.info/content/song-pelinal. In short, he murdered any and all Elves he could find, simply because they were Elves.

KOTN has nothing to do with murdering elves, though. You could as easily regard it as a quest to turn the evil that Pelinal had done into some final good. It is a noble endeavor through and through.

Wouldn't recommend Morrowind. Combat is so insanely bad, and the graphics are poor too (even for its time)

Yes, yes for all.
KOT9 is perfect for your type of character and well, there isn't much to say about Oblivion.
For there are no words to describe it.

Words to Describe Oblivion
Good
Letdown
Vast
Dull
Mysterious
Large
Immersive
Timesink
Broken
Sparse

its good for that character and the fort for fighters would fit him well too. nothing like your own keep. though shivering ilses would be odd for your character. though for that type of character i would say morrowind might have three factions for him. imperial legion, temple, and imperial cult. most of the rest of morrowinds factions have a sort of self serving or political light to them, thouh they are more realistic reasons then doing good cus its not bad or vice a versa.

Most of the DLC is missable. KOTN is good, but Shivering Isles is the best thing about Oblivion.