Killing some of the DB contracts felt awful. ;_;
Especially because of what happens to Tova Shatter-Shield.

I felt like a jerk through much of my Stormcloak playthrough. Didn't like killing the soldiers, betraying Baalgruuf, putting the Silver Bloods in charge of Markath and removing Idgrod after she helped me at the Thalmor Embassy - by the end of it I refused to kill Rikke or Tullius and let Ulfric handle those two.

(I didn't much care for putting Maven Black Briar in charge on the Imperial side either but Laila Law Giver is a pretty piss poor jarl so it didn't bother me quite to the same extent).

I hated the shopkeeper shakedown in the TG and many of the quests there, at least until Karliah showed up.
I felt pretty bad about most of the assassinations for DB too. On the character I took through those two questlines I pretty much had to turn off my empathy gland.

I still haven't managed to get the Oblivion Walker achievement because, whilst most of those quests are fairly benign, there's no way I'm killing Erandur or becoming a cannibal. I did do the Boethiah quest and didn't like sacrificing a follower, though the rest of the quest is fine. I hated beating the priest to death for Molag Bal, even if he was a bad guy. I tend to take the view that some people probably do need to die but I'd rather give them a clean death if possible.

I guess this just makes me a balanced human being.

Really??? He was having you exicuted for being in the wrong place at the wrong time while you innocently were crossing the boarder.... he's pond scum..

This, too. After the battle for Whiterun, I felt bad. On the other hand, removing Igrod made me feel like true scum. I liked that woman and her family so much.

This is why I most likely won't do the Stormcloaks questline in the near future. Even though the Imperials didn't seem like the nicest, most of the Imperial jarls were pretty fair.
Sure do beat Skald the grump, Laila the really oblivious or What's-his-name of Winterhold.

Oh nice!! that should make this quest much easier in the future

no, i have a great hatred for humanity, i likely wouldnt feel bad about actually killing someone, so definitely not in a game

Yes. Yes, it does.

One of my accidental murders on my 1st character was on a Stormcloak soldier I accidentally killed in one of the battles, but the rest didn't turn on me. You think the 'excessive' manner in which you killed him/her made the difference?

More convenient...not easier. As dookie0311 pointed out: "that place SUUUUCKS". Also, be advised more Falmer sneak in from the hole in the wall after you think you've cleared the place.

I'd feel bad for Malkoran whom I first soul-trapped. Then I soul-trapped his Shade. Then I thralled him. He (and his Shade after that) has died about 10 times now, and I still keep resurrecting his dead body to serve me all the time.

That is, I WOULD feel bad to him if I was capable of such feelings. I think. Anyways I think he's close doing a world record in dying.

I felt bad when I did the Namira's quest. Espeacially when I took all my $ back after taking a chomp out of him for a ring. I wanted to kill everyone in the room after. I might still do that. Also I wanted the werewolf kill for the Hircine quest, so I slaughtered all the hunters so I can one on one him. He had a sliver of health left, it wasn't worth it. Then the 1st horse I bought got snacked on by a dragon. I wanted my $1000 back. The worst was when Lydia died. I keep telling myself that it's was the Dragon Priest that killed her, but I know it was my errant magic spell, or the Fire Atronarch I summoned. I gave her a proper burial in the priests coffin.

The Dark Brotherhood. All of it, from the moment you meet Astrid to the end, every quest. Some were more messed up than others but they all made me feel like pond scum. I wouldn't have realistically completed the questline, but the alternative was to create another character, and I was already 250 hours in and wanted to wrap it up so I could retire my character. I did try to temper it by not killing Maro (we were even. I figured), Cicero, Nilsine, or any guards or bystanders that I absolutely didn't HAVE to kill. Still, though. Pond scum.

The only part in the entire storyline that I enjoyed was the part at the end where you kill

Killing Parthy for that witch, Delphine.

As if they ever got to know it. On the other hand, only I could've been so stealthy for them not to know it. So they kinda know it anyway because they didn't get to know it.

The "Hired Muscle" jobs.

The Companions- Honor, Glory, and beating up women.

Understood.

There's one where you beat up a woman? I guess I didn't do enough of the radiant ones to get that one. I only recall beating up the inn keeper in Riverwood.

If you haven't done them, save them for last and save the game. Then do them both to get the achievement and go back to the previous save, then don't do them.

That made me feel so awful I could have cried! It was like, giant statue of original falmer, can't you see this amazing, precious thing?! Why would you ever damage something so important for money?! I tried to put the eyes back in but they would'nt go.
I tried to drop the eyes but for some reason I only dropped one. I was in a rush to get the horrible quests and trophies done.

I also thought, why the hell is this awesome statue in this hideous quest, what a total and utter waste. It should be for all to see.

I felt a bit bad when I found out Tova kills herself if you kill Nilsine. I spent a bit of time wandering round the house looking for a living female, for Blood On The Ice. The third time looking I found her dead.
But then I thought about how badly they treated Miuri, and thought, well I did what she asked and they clearly hurt her, it's done, no point bothering about it.

I stopped being bothered about killing Gaius Maro when he was rude to me while going near him while thinking up ways to kill him.
The third time I said, screw this, you're dead you obnoxious jerk. Felt a bit bad about destroying his reputation though. Not that bad, though.

Killing the Priest of Arkay for Namira's quest, A Taste Of Death.

Pretty much BOTH sides to the Redguard/Alik'r feud.

Several - depending on which one "pops". Before I decided I couldn't bother with the Companions, I got to beat up Adrianne and another woman (can't remember who now - LONG time back....)

You beat up a woman as the first Companions quest.

Feels odd, but this is Skyrim after all.

The only thing that's ever bothered me is the shakedowns at the start of the Thieves' Guild line, especially since I tend to have more money than Croesus and could easily pay their debts off for them instead.

OK, there is one other thing- Aventus Arentino. That kid is a little too happy when he finds out you did what he asked, even though the target thoroughly deserved it. Creepy as hell and makes me want to take him out too, the Tenets be damned.

I'm guessing while playing a female character?

Both of my characters (1st one male; 2nd one female) I was sent to beat up the guy running The Sleeping Giant. Were they both random, but coincidentally the same one?

I was asked to beat up Belethor. That felt quite good, actually.

Concerning the topic, I always save, and try out a lot of options before doing things. I reload and try a different approach if the result doesn't appease me/doesn't suit my character. And as I'm playing a 'good' character, there's not much I can do that ethically rubs me the wrong way. Shaking down those shop keepers for the start of the Thieves' Guild wasn't very fun 'though. And the first real quest you have to do for them is still on hold, since it isn't much better. But I'll get to it sooner or later, otherwise I can't take over the guild, and as a result get power over Skyrim via the underground community.

I tend to feel like a bit of a jerk whenever I have something that I can't kill at my current character level such as a dragon or giant so I run to the nearest settlement for help, only for the townsfolk to all attack it with their little iron daggers and get absolutely annihilated..