I want a challenging playthrough. Any ideas/ways to play/character ideas for playthrough/stuff you guys have tried/etc. Anything along those lines would help. Thank you!

Post!

Play on master and dead is dead. Or try the naked nord challenge.

play as a vampire necromancer. Challenging and fun.

try this

http://www.gamesas.com/topic/1328262-remaining-on-level-1/

try playing as a boxer

Step 1. Exit Skyrim

Step 2. Buy Morrowind

3. Play!

Now there's something fairly challenging.

use no potions, only food, and use you fists.

Try a no-stealth run. Or swear off of one or two of the crafting skills. My current character isn't really using alchemy at all, and has enchanting and smithing gimped via a rebalance mod. It's almost a challenge, only real problem is that I'm at the armor cap even with gimped smithing (went the heavy armor route, maybe light would be a better choice.)

Also, for a combat challenge, play a dual wielder or two hander but only use critical strikes (attacking while sprinting.) It takes a bit of skill to gauge the right distance. My two hander went this route, basically you go for high stamina, low health and armor, and sprint away from enemies until you can line them up in your sights, then rush in with a sprinting power attack.

Master Difficulty.
No enchanting.
Stop Smithing at 80. ( level it normaly ie.. twice your character level until 80)
No companions.
No potions.

Be the highlest level vampire, do not feed and play only during the day.

Use a pickaxe and mine your enemies. ;]

Master difficulty
No enchanting
No smithing
No alchemy
No companions

Do Peryite's quest, The Only Cure, as close to level 12 as possible.

Thanks guys!

AAAND Fight with one hand tied behind your back. ie no dual wielding weapons/magic. No shield. (or just Roleplay you lost an arm.)