I'm not going to brag about a game or think I'm one of the best players but I've played skyrim since it was released and like to consider myself hardcoe. I've played every single race and every single class imaginable. I have two different lvl300 characters and probably over a dozen lvl81s. I've been an archer, an assassin, a fighter, a spellsword, a pure Mage. I know all the tricks most of us probably know for creating uber weapons and armor. My preference is to do that since I've long considered TES to be meant for gaining in strength as you level till you become one of the divines practically. But I also occasionally play naked and with no gear at all on high difficulties just to prove I can do that too.

But what is a hard challenging way to play skyrim? And I'm guessing the hardest with my play style (I.e using smithing, alchemy, and enchanting to slowly build your character to epic proportions). I didn't even know for a while when I started that you could change the difficulty. So when I started starting over for other characters I would usually switch it to expert difficulty at least but only switch to master by like lvl80.

So here's what I'm doing now. I started another character and am beginning the game and playing only on master difficulty. Then when I get to lvl50 I will switch to legendary difficulty and fight all the major bosses then until I reach lvl80 to fight the ebony warrior (though I've already beaten him on legendary at that Lvl without "cheap" tactics in my view like using the marked for death shout, or using followers or pets or stun locking or sneak attacks).

Of course the actual hardest would be to begin on legendary, only play on legendary, and try and do all the main quests and fight Alduin, Harkon, and Miraak by like lvl20 on legendary.

But legendary difficulty was only added with the new edition that added the ability to surpass Lvl 81 and play on such a difficulty. The traditional hardest is still master. I just want turn it on legendary early by Lvl50 to make it harder.

So this is MY challenge. Right now I'm lvl18 on that character playing as a spellsword (heavy armor, one handed, destruction, restoration, blocking, smithing, and conjuration perks so far). The hardest fight for me so far was going into Volunrud (however it's spelled) early and encountering a draugr death lord archer. Those enemies are a pain on high difficulties for ANY level (even on my Lvl300s, I've encountered three of them at once one time and they put huge dents in my health before I finally killed all of them). But I was certainly not expecting to encounter and fight one on master at just lvl18.

This is my challenge then but I know there's far harder ones I doubt I could do like starting on legendary difficulty and only using your fists fighting naked without armor. You get through the first 30 lvls and I will bow down before you.

But now I leave it to the rest of you to come up with hard challenges for the rest of us to try.

Battleaxe Barbarian:
-2 handed weapons for combat, bows only used to hunt for meat and hides
-little to no armor (I wore ragged trousers, basic boots and hide bracers)
-no potions, only meat and mead to heal
-no magic of any kind
-no enchanting or wearing of fancy enchanted gear (talos amulet for RP or something similar is ok)
-no alchemy but can eat raw ingredients like hawks feather to cure disease
-can smith but can't use anything beyond steel (I used an iron battleaxe for most of the game then a Skyforge steel battleaxe)
-no helpers unless forced to for a quest

This is a challenging build that I've enjoyed completing the MQ on Adept, if you're feeling more hardcoe then you could try this on Master or Legendary if you enjoying dying alot

Hard challenges are for pussies.

YOU NEED A NORD CHALLENGE

(Only use your fists, only heal with meat, and mead)

Although they sounds challenging it also sounds boring to me. Not for me

HUDless

Expert or above

No healing or stamina potions allowed.

No healing mid battle.

No music

Throw in a few mods that make combat more difficult, SkyRe should do the trick. If you play on master difficulty crossbows will one shot you like it's nothing, and one miss-timed block will result in your guts all over the floor. Even on adept (the difficulty you should play it on) it's still very difficult. Also, give yourself some restrictions. Play a Wood elf hunter that can only wear leather, scaled and dragonscale armor, only use bows and daggers and has no idea how to use magic, how to enchant items or how to improve metal objects. Skyrim is a lot harder if you can't upgrade everything to be double as effective and enchant it to give you crazy stat boosts and additional damage.

The (nearly) sneakless sneak:

Expert or higher

No perks into sneak skill, only skill ups

Magic allowed: 2 schools max but not destruction.

No poisoned weapons

Can only choose either enchanting or smithing not both

Must use a mix of heavy and light armor *which piece does not matter*

Armor above ebony-level is not allowed, weapons are fine

Potion count cant exceed 30 total

Pre-enchanted gear not allowed to be equipped

Bows/cross bows allowed but cant go higher than dwarven

No weapon type restriction

No shields above dwarven level

Alchemy is allowed

I'm pretty much in line with all of this. I am a full supporter of SkyRe and play on Master all the time.

Addressing the super-uber-duber OP'd gear... You have to actually go out of your way to do some of that. I will improve gear to legendary and then stop. I don't think the game was initially intended for weapons to be continually increased. Enchanting has a cap, your AR has a cap. Improve weapons to Legendary... and stop.

haha mine was a Nord based build, all I have to do is drop the axe and put up my dukes

This. Add the Battlefield and Injuries Mod (and/or First Aid mod) but don't take advantage of any of the NPC healers available with this mod. Basically, if you sustain a grave or life threatening wound, you're going to have to get real creative (and lucky) gathering reagents etc to make bandages to disinfect and heal your wounds. And get LOTS of rest between battles.

Which means you'll have to add game changer exposure mods like Frostfall and Wet & Cold to your mod deck. It's really difficult for your Dovahkin to sleep in order to heal/cure themselves from grievous battle wounds when they're freezing to death. Or try to hold a conversation with an important quest related NPC if they're freezing to death......

Perhaps consider adding personal needs mods like RND (or IMCN) which require you to eat, bathe etc. Lack of proper daily nutrition, food poisioning/disease from eating raw meat, and lack of personal hygiene will affect your crafting, combat and stealth skills. And can add to disease and infection of your wounds resulting in death....

Add food mods like Wolferoo's cooking recipe bundle (80+ food recipies), Sate that Appetite, Be a Milk Drinker, Bert's HF dairy goods (lets you milk farm or wild cows and goats for edible/craftable dairy products) and Morrowind-Oblivion Beverages. These add many various beneficial/cursed buffs to foods your char eats. So your char is forced to eat selectively. If they can't find nutrious food to cook at a fire pit or dairy products, then they'll slowly begin starving to death. And their battle skills will gradually be negatively affected over time.

Add a wildlife mod like RWS, and Hunterborn so your char can become self sufficient i.e. won't need to enter the city holds, towns or villages to buy food. Force them to forage and live off the land in a hunter role while adventuring.

Add a NPC behavior mod like Immersive Patrols, which adds roaming patrols of brigands, Imperial/Stormcloak patrols, merchants, hunters, vamps (with a VL who will hunt your char around Skyrim until you defeat him. Then mod spawns another). You'll meet these randomly on the roads and off road in the wilderness.

Add a game changer mod like Civil War Overhaul, which can literally make your char's life a living hell if they opt to pick a side in the civil war. Certain holds, towns, villages, and NPCs you encounter in the wild can have Pro Stormcloak or Imperial leanings. So you may find your char is welcomed or treated neutrally by guards of the Pale Hold. But find himself running for his life if he forgot to remove his military armor and tried to enter a pro civil war faction hold like Solitude or Windhelm.

Get to the points in the game where you've initialized all 3 DLCs so you've got a nice variety of flying lizards, bloodthirsty flying bats, and lonely dragon cultists stalking your every movement around Skyrim.....

Lots of creative ways to make your char struggle to live before they die a miserable death with mods like these.