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So I am going to finish the mages guild and main quest. I've already done Ko9 and fighters guild.

My question is on the shivering isles. Should I start a new character or just take my character from tamriel and the mainquest?

I found that I had the most fun with SI taking with me the least items from Tamriel, so I had actual use for the low-level gear found there. Character level didn't matter as much, though I guess the immediate lack of gear could become problematic starting out at level 15 (or so) and higher.

This one playthrough I RPed a character that got stuck a prison somehow (the real one, not the game start) and thus lost all my gear to the jailor. But I managed to escape with my last lockpick and I was on the run for the guards. I was wandering about from one hideout to the other, living off the land and such, until I 'heard' of a strange island that seemed pretty far away from all the coasts. I decided to hide away there, but then of course I got trapped in that weird dimension and stuff.

What is K09? Some mod?

Tricky wrote:
What is K09? Some mod?

I'd say he means Knights of the Nine.

If your character is a goody two9-shoes, and having played through Knights you probably are, then it will be difficult to role-play the character in Shivering Isles if that matters; or at least it was/is for me.

You could try playing a necromancer, there are even mods out there that let you do that, including a mod that allows you to switch sides and join Manimarco's Order of the Black Worm. There's also Necromancer's lair which I find fits into an evil mage play through.

Set up the character as a mage as suggested before, race and birth sign can be any. I'd also suggest some of the other mods if you're going for another play-through. The main quest can of course be completely ignored if you wish. Joining the Dark Brotherhood and maybe the Thieves guild and you have a completely different experience to your first play through. The best evil run through though is to actually do the main quest but running over into the Servant of the Dawn mod, which allows you to also switch sides and become Mehrunes Dagon's representative on Tamriel.

Servant of the Dawn is incompatible with Knights of the Nine by the way, as it should be IMO. If you want to use it, and everyone who wants to play an evil character should try it once, simply disable Knights.

I'd also recommend the best role-playing mod I've ever come across as well Heart of the Dead. Note the mod's requirements though, you'll need other files as well for it to run.

I played Servants of the dawn, it's a good quality mod. I didn't know there was also an opposite side mod to the Mages Guild quest though. The Heart of the Dead mod seems cool too. Sadly though I've had quite my fill of this game. Replaying a bit of Morrowind though, every now and then.