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So I've started a new game with the combat difficulty all the way up just to say I could complete 3 guilds and the main quest before level 50, and so far, I've been doing fine by sneaking around and then sword-and-shielding it when things get hairy. Because draugr are lazy bastards that forget to wake up before Cogan the Barber comes by and kills them, my level us now nearing the double digits and my stealth is in the high 50s/low 60s. Now, this sucks, because stealth is not at all how I go about murdering people, and the level scaling system seems to be blissfully unaware of this. However, I can burgle like a champ, and I'm pretty damn good at the lockpicking minigame, so none of the houses in any village I go to have any food left in them, and Alvor still doesn't know where all his good shit went.

Unfortunately, because I was dicking around in the middle of nowhere instead of pushing the plot wagon, I'm now running around at late level 8 with underpowered gear, and wouldn't you know it, I've come home to Whiterun after a markedly premature encounter with some Draugr Wight Wizards, and a magical surprise attack by a wizard lady who didn't like when I broke into her basement and stole everything. (Should've murdered her first, that atronach-summoning twatwaffle!)

Point is, I'm out of food and drink, and three thugs are always murdering me outsude Whiterun. I do not have a shield big enough to block all three of them when they gang-rape me, and I do not have enough health-replenishers to kill them all. I only have 100 mana because Cogan the Barber takes no stock in petty wizardry.

I have 3 questions:

1. Will they despawn/disband if I run off, lose them, and then steal all the food from Honningbrew and all the fishing shanties before coming back to kill them?

2. Are there any good corners around Whiterun (or in general, anywhere arounf Skyrim, since this isn't going to be the last time someone catches me stealing and I've failed to prepare for level-scaling threats) to trap man-sized NPCs just within killing distance? I'm willing to plink away at them for an hour with my 0 archery skills if that's what it takes.

3. These would be the first full steel sets of armor I've seen all game. Are they at all worth upgrading from banded iron, in practical use or in their pawn value?

Skip steel and go straight for ebony when possible (by selling the steel, should get at least one decent ebony piece); I usually run back into Whiterun if thugs are the case so I can loop them back to Dragonsreach / the Companions.

I'm at that weird stage in shop spawning where Ebony never shows up. I only get magical dwarf armor and magical orc weapons, which as I understand are only about +1 higher than Steel in most aspects.

Skyrim?

I probably have more characters in Skyrim then you have max health right now...

260 health, now that I've kited them off to the companions and run off the level-grind heavy armor and Block on the mudcrabs. (320 more often than not, since Hogann is clinically addicted to health draughts) 

I'm assuming that you have no poison.

I sold all the good shit, but I do have the fat bottles of Paralysis because they're goddamn hilarious.

And you are not yet the Dovahkiin?

What is your primary weapon?

Nope. I decided I wanted to be leader of The Companions/Thieves guild first, because Cogan is an RP-heavy character, and it makes more sense from a world-building perspective that the Greybeards send for him because he's famous in the area and has been seen eating dragons.

What's your race?

I'm assuming that you just have a plain iron sword/shield.

My race is a long, five hundred miles around a deadly track in which the cars rubber will be peeling off from going at such blurring speed while the audience yells to go faster.

Minnie, I'm trying to save a Barber's life. This is serious.

Get your puns out of here.

*Sigh*

Punta Claus isn't coming this year I suppose...

*Leaves dragging a sack full of puns*

That's just Sackrilegious.

-_- you wanna go

Are you sure you're up for it? You got utterly sacked the last two times. I have this victory in the bag.

You're garbage at pun-making, Sent. I'm the punlord and you're a guy who sits under a bridge selling bagels, so you'd better return to your spot or else another cabbage munching fucker steals your spot. Leave before I send my gorilla to teabag on your face, go pack your bags.

Bolding words spelled within words don't count as puns, they count as forced garbage.  Speaking of, I've bin thinking, why are you the one who gets crowned king of puns, when I'm the one who's trashed foes in pun combat before you even joined. (*See the Honor4Ever wars.) I guess I have left the crown up for grabs. If you can't hold onto the title, however, (And I'm not sure you can.) you should just garbag where you came from.

Don't get saucy with me fuckboy. I'll beet you to a pulp and romaine king of puns, so lettuce laugh at Sent's awful bad puns.

Lettuce isn't part of a sauce, you Anal Cunt. Your pun career is about to suffer a Megadeth. You've been failing Duran Duran this whole conversation, and you'd have to be a Def Leppard not to hear how shitty your puns are. I don't AC/DC how you could think you're any good at this at all.

That was just terrible. I'm not even mad anymore. Just dissapointed.

Shame on you, Sent. You just killed the mood.

You have no taste in music, and I won. HA.

Nah, I whooped your ass. Guess you could say, if they made a movie about this, it was 'bassed' off a true story.

Besides, how did you win, I never quit. But I suppose you do deserve a 'metal' for trying.

You did quit, right during that post. Though I guess I didn't notice you put song names into your posts because usually you're very blatant about it. (Which, frankly, someone as forced as you needs to be.) Switching themes in the midst of a pun battle is among a long list of dirty deeds which you've exploited to postpone the moment when you're shot down in flames, because you know it's such a long way to the top. I'm afraid this is a touch too much. You have to face the facts: You may think you have big balls, but you're really just a charlatan on the highway to hell, and you'd better find a place to hide, safe in New York, before I bring some Rock and Roll Damnation down upon you for your high-voltage dumbassery, you little squealer.

What the fuck are you talking about? My puns hold the roof up! Your jokes are garbage, but I guess don't stop believeing. Now, i'm gonna go dance all night to the best song ever over my victory. Bye.

You didn't even stick to the same band, so your theming is shit and your puns are irrelevant and lost. None of your pun aspects except the fact that they're musical come together cohesively. You've been livin' on the edge for too long, and nobody here was jaded enough to put you back where you belong. Meanwhile, I'm back in the saddle, tossing you around like a ragdoll, and you can't even tell when you've lost. I mean, if you're really crazy enough to think you won that, dream on, I guess. I can't stop you, but I'll still have the crown.

*Swats your hand* This crown is mine, bitch. You'll never win. But when i'm gone, don't cry about it because the crown is gone. I'm suprised you stuck around so long to be honest. And the big paragraphs aren't really helping ya much.

I think they are.

Puns made by Sent: 27.

Puns made by MinnieKing: Maybe 9 things that could qualify as puns, or even remotely clever wordplay at all.

Gotta say, your argument about defending your crown just doesn't hold water, because it looks like the crown is on my head already. If you think for a second that TL;DR excuses your ineptitude, you're all wet. Your puns are utterly vapid, and I'm afraid this all really boils down to one simple fact: You're all washed up. Maybe sea a therapist about your delusions.

Puns made by minnieking today: at least 10000, so get off my ass.

Water puns, really? Those are the lamest of the lame.

Only the ones in the battle count. A king can have a thousand shitty soldiers all over the kingdom, but if he only has a few guards in his castle and the glorious tyrant comes to smite him as he's unprepared, then he still loses the throne. I'll get off your ass when I'm done riding into Pun-Jerusalem, where my loyal subjects are greeting their messianic wordplay pundit with joy and admiration. 

Besides, at least I'm still making puns that are recognizable as puns.

My castle is in the sky.

A Castle In the Sky...

Now you're just naming songs to name songs, you're not working them into what you're saying or anything. This is absolutely reprehensible. For someone who's apparently sitting in the Laputa pun luxury, you're not making many quality puns.

Fucking loser. I'll punch you senseless, you puny punctuating punk. You should be punished for stepping up to the pun lord, back down before I puncture your face as a Halloween pun'kin.

Just because you overpronounce the word pun in everything doesn't make it clever or of any use against the beefy bullwark of puns I have laid out before you. You're cowed out, pasture prime, and the steaks are too high to let this pun offense go.

Pffft. Amateur hour. You're a pile of bullshit. Let ox observe Sent, once again failing to make decent cow puns. I'll have my best soldier, Sir Loin attack you.

He's an Argonian, driven out of his homeland due to the fact that nobody he knows has any hair, just weird feathers and shit. He has journeyed North endlessly in search of hairier people.

I stole a steel sword and shield (Made "Fine" with stolen steel bars) from Alvor

Okay, first off:

Fuck yo bitch and the clique you claim.

You need bow skills. Sneaking and archery go hand in hand. Hell, if I remember correctly, there's a sneaking perk that multiplies sneak attack bow damage. Practice on sleeping Draugr.

I also advise light armor. Get the nightingale armor (or Shrouded, if you're like that) as soon as you can, as wearing the full set is basically lighter ebony. Lighter armor=Faster and Stealthier.

Now, here's what you can try:

Be as close to the guard as you can when you're attacked. Their hivemind should automatically alert all guards in the cell. The thugs will have a "bounty" on them in that Hold.

Add paralyze poison onto your sword. Hit a guy. The guard will take care of the rest. Repeat.

When your health is looking a bit dire, use the Histskin ability. It boosts your health regen drastically (ten times!) if you're an Argonian. Use it wisely, though, as you only get one chance a day.

Cogan does not believe in bows. They aren't his idea of a Manly Weapon. Much like the barbarian he's based on, his technique extends to the "Spray and Pray" that people use in battle formations and not man-to-man combat. He does not sneak and snipe: Bows and arrows are merely fuel for his Speechraft skill.

Basically, he's going full shield/sword/heavy (After a certain number of perks, Armor doesn't make that much of a difference in sneakery iirc, as long as you wear no/light shoes.) and then slapping on some restoration to run away with. He has quite a few restrictions on weapons, actually, since the original Cogan was an unarmed build in Daggerfall, where you could just add restrictions any which way you wanted in exchange for perks and skill points. Since unarmed is utter dogwank in Skyrim, though, I decided to make him heavy-shieldy in order to feck shit up the same way. (And also get the only unarmed buff in the game.) To maintain bragging rights, I'm still going to say that Cogan isn't sophisticated enough to use bows and destruction properly, and restoration was just a necessity.

I think the Elder Scrolls games are the only games I really play anymore...

I love the games to death, though I'm hooked on Daggerfall right now. 

If I remember properly, the lady you stole from should be a witch. I've read somewhere on the Skyrim wiki that the thugs are sent either by the witch you stole from or one of her witch friends. If I remember correctly, there was a letter in that basement addressed to a friend which you weren't supposed to see. Hence the reason for her sending thugs after you to keep you quiet.

P.S. You deserve it you thieving little no good Dovakhiin. I hope you learned a lesson to never steal from others. ;)

Edit: I don't know if those thugs will ever stop harassing you, but as Tim suggested stick close to the Whiterun guards if those no good thugs decide to kill you.

Cogan prefers to steal what he needs and cannot afford, because it is preferable to murdering people. But since this witch in particular hates him that much for giving all her cutlery and secret witch documents away to some random douche in a beer factory, then he is going to murder Anise with his bare hands and reload the save, until he has done as many back-breaker fatalities on her as the amount of save restores I had to do to deal with those asshats. When her other hagraven friend inevitably sends thugs for that, his revenge will rage on! Not only will Cogan steal all her shit, but he will also steal her heart, steal her ring, and also have become a vampire for the explicit purpose of stealing her whole fucking lifeforce!

COGAN'S BARBEROUS, ALCOHOLIC RAGE KNOWS NO BOUNDARIES!

If anyone wants to murder Cogan, they should do it themselves and not get innocent bandits involved! What the hell's the deal with people giving legitimate employment opportunities to thugs on the street!? And why can't they give Cogan something productive to do!? This is why he's been swept up into the endless penal system and embroiled by complete accident in the affairs of the Riften Mafia!

Always thought that was a nice touch with that witch and her hagraven sister.

Though it might have been cooler if she had sent Forsworn fanatics after you instead of regular thugs given that she was a hagraven.

It woulda been a pain in the ass for low life rogues like me to deal with them. I hate having to spoil my beautiful Kahjit claws.

Umm...

Well, if you really are interested in revenge, then LEVEL UP!!

Go clear out some dungeons and maybe you'll find some cool armour/weapon shit. Oh, and if you've gotten into the Companion's inner circle then you should have Lycanthropy(Allowing you to transform in a werewolf for 2.5 mins). Also perks (by praying, drinking potions, etc..) should make your life easier. 

Finally get you filthy Argonian ass up to the College in Winterhold. You should be able to buy spells for cheap at the entrance*.

*: When you try to enter the College, you will be asked to demonstrate magic in order to enter, If you don't have any of the required spells, you should be able to buy them for real cheap. 

Cogan doesn't believe in magic, or bows in most capacities, so he only uses natural abilities and physical attacks. (Except for level-1 left-handed restoration to get out of scrapes he can't deal with. He doesn't know where he learned it and believes it to be a biological feat.)