I've been thinking of getting back into DiD, because it encourages me to try different things and see how well it goes. And I was thinking of starting on expert, perhaps. But I want the combat to be ending pretty quickly and make it similar to Dark Souls kind of. What would be the best way to do this? I was thinking of starting with making an executioner who would use a two handed axe and would wear the dark brotherhood mask that the captives wear at the abandoned shack.

I was thinking of perhaps setting it to Expert and wearing light armor, but make use of the fortify restoration loop to make some sharper( but not ridiculous) weapons. I want to be frequently on the edge of my seat. Would Master be better? I have never played on it before. I remember having a level 1 Argonian Heavy Armor warrior (this one wasnt DiD and was on Adept) and a level 1 Khajiit hand to hand serial killer,(Expert) and both of them could do ok, but two handed users absolutely destroyed them. If they didn't get OHK'd from power attacks, they'd be at like, 2 health. So no doubt Master may murder me.

I like a good swordfight, but I'm eager to switch things around a bit. Man, I wish my computer could run Skyrim T_T

I was thinking more along archery. Those bonuses can get you through fast.

I've only played DiD a few times myself andI can't speak for anyone else, but I would never play DiD on master. The reason is simple, sabre cats and cave bears, I'm serious, okay maybe not entirely, as this also goes for frost mages, and as you said, 2H'ers.

I think master is a bit high for low level characters, let alone DiD accounts, unless you truly want a, "quick" play through, as in getting taken out on your way to riverwood.

I recently played a semi-DiD high elf on expert,(as in saving very rarely, a couple levels apart until level 10) because I'm really not a big fan of watching the opening and remaking characters every day, I just don't have time for that. But I digress, the difficulty worked well, suspenseful, but she could take a few hits without dying,(save 2H weapons) so the play through felt very balanced, and I ended up using different tactics than usual such as illusion to keep her from dying by withstanding the heat of combat against high level enemies.