So i have a total of 100+ hours combined from two characters. Now i find myself starting another character. Is there something wrong with me? I get into the game every time i play it but after awhile it becomes tedious. Help? Anything to freshen up the experience? Role Playing guidelines/rules?

I know i can count on the great people on this forum to help me out.

I'm the complete opposite.

Cheers

When you get to tough parts or are stuck fighting enemies that kinda counter your playstyle, for instance ice wraiths are impossible to assassinate or even hit, just push through like you are your character and want to get stronger so you can face those situations better, or just enjoy the challenge and chance to do some critical thinking about the situation, and ways you can attack it.

Forget the quests for a while and just explore. That usually works for me.

I think with my new character i'm going to completely stay away from the main questline and mold him onto a sellsword/wanderer. But i will start sellswording and wandering after i serve my time as stormcloak soldier.

The game has a lot more to offer then just dungeon crawling, and maybe that's your problem. You didn't really state what you've completed. There is an entire world to explore, books to read, people to talk too, tradeskills to mess around with, and god knows what else.

Perhaps try with your next char to a) not rush, use "useless" perks, or c) read into the culture a bit more.

Honestly, I can spend hours just reading through all the books, talking to towns people and organizing the crap in my house (yeah, I'm a bit OCD about where everything is). Sometimes, I don't even get to go out and quest. I wish I could setup shop and sell my crap all day long, yeah be a bit simcity-ish I guess, but would be cool nonetheless.

You could rp too, I do that a bit, but nothing major or in-depth. My wife just thinks I'm "thinking out loud". Might want to try and curb your playtime too. Maybe you just playing for too much at a time, and not able to enjoy it nearly as much. Remember, absence makes the heart grow fonder, and it works for Skyrim too.

I've spent 7 hours on my new character, and I haven't touched a single quest. Just go out and explore the world. Get a follower, pick a direction, and go.

I've stuck 50 hours each in two different characters, but wasn't quite happy with either. In the end I rerolled as a Conjurer with a bound bow and pets, and I haven't been happier. But I wanted to play as a mage from the start, didn't like destruction, and tried a sneaky archer and a paladin instead. Both characters were very powerful, but not quite what I wanted to play. So you are not alone

I say it again..
Am also creating alot of alts.. on my probably 10th character now (lol)

But one i always find fun playing is my pure warrior... No extreme armors.. no maxed enchanting/blacksmithing (0 points in both of them)
General rules i have for this character is.. NO magic what so ever.. No magical armor / equipment either.. Potions ofcourse..

Use what you loot.. If its magical, sure use it until its empty.. No recharge

(Yes its doable in this game, believe it or not )

I have started over multiple times, and now I have finally settled on a character type. My advice to you is to start running around exploring, and trying out different styles. If you don't like the style, then start over and try something different. Keep doing that, and eventually you will find a style that you enjoy, and even restarting won't be that much of a problem.

My question is: why wouldn't you want to start over with new characters?

If you're RPing, then it's pretty much a necessity to try different things. If not, then there's still the issue that combat--a huge percent of game time--is only a challenge at lower levels. And there are different approarches to the game that require different character types. You can do a pure mage, pure fighter, pure thief, then combine different aspects for each for more characters. That by itself is worth multiple restarts.