Lately, I've found a lot of enjoyment in making my characters seem like underdogs, rather than overpowered 'hey look at me' superheros.

My Bosmer warrior currently wears plain iron armor, no helmet, and a Whiterun guard shield. And while he has come across several steel, Orcish, and Elven weapons in his travels, his sword of choice is a simple, non-smithed iron sword that he received in Helgen. He doesn't carry more than a few health potions, and doesn't resort to any magic other than healing spells. I purposefully limit his armor and weapon so as to feel weak in a fight. On Master difficulty, he is essentially a pushover to several enemies and is in constant fear for his life; even mudcrabs show no mercy.

The game has become an incredible challenge and makes me appreciate every victory over my foes. It also just makes the character seem much more humble, as the armor he wears is nothing special or exotic to Skyrim's population, and he doesn't scream "I'M THE DRAGONBORN!" Obviously, in a game that practically throws fancy weapons, armor, and strength at you, it isn't quite as tempting to feel weak, but it is incredibly exhilarating. I was wondering if anyone else plays this way, and if so, what is your setup, and do you even take it a step farther?

I don't play like that, but I'm glad you enjoy it.

Whatever floats your boat.

I've done this with a few characters. My current - I rp that he's cursed, and needs dragon souls to cure himself. This means that I only level him when I get a dragon soul. He was really, really weak in the beginning and that was a fun challenge.

I also had one dead-is-dead character who was blind, which means I had to navigate the environment in a different way. No - I didn't turn the monitor off, but I tried to play as if she really couldn't see where she was going. This meant moving slowly and carefully, avoiding deep water, not setting off towards that interesting ruin at the horizon... etc. She could not read skill books either. Spell tomes was ok because I rp-ed that she could sense the magic, and learn the spell that way. It was also very interesting.