I'm a complete idiot at leveling up (blame my lack of playing legitly in a long time) and now i've found myself about halfway through the main quest and a hero in the arena (with only an iron sheild, longsword, and helmet might I add) and i'm only level two. This presents a problem considering that I plan to sacrifice the Mace of Molag Bal to Martin since I don't use blunt weapons, however the quest requires that I be level 17. Any tips on picking up. By the way I play on the easiest difficulty (blame my lack of the idea to make it higher before I start my first legit playthrough in quite a while). I'll gladly post and info needed if necessary.

Several ideas come to mind.

Most directly to your question: Increase your major skills until you are level 17. If you need tips on leveling up any particualar skill, ask away and plenty of folks can help.

You might consider just giving up Sheogorath's staff at level 2. Simple.

You might consider just placing the silly main quest on hold until someday your character achieves level 17. There is so much other fun stuff to do in the mean time.

Leveling up quickly generally leads to regrets by characters who start getting their butts kicked when their killing skills and supporting attributes start falling behind their foes. A slow and careful leveling plan can help prevent this. Having the difficulty slider set to easy can actually indirectly aggravate things; when the game is set to easy, it requires less spells/hits/arrows to kill your foes so your critical killing skills level up slower because they don't get as much use. You get 10x the leveling to your blade skill by taking 20 hits to kill a foe instead of 2 hits. That is also a good reason not to use overly powerful weapons or spells when trying to level up those killing skills. Slowling killing a foe with that little flare spell advances your destruction much faster than a very powerful spell would.

So basically just bring up the difficulty and use the worst weapons I can find? That and I could just give up Wabbajack and then go and take it from the testing hall considering after Shivering Isle i'm the Daedric Prince of Madness and roleplay wise (I rarely roleplay the game but occasionally I roleplay out events in the story) I could probably simply remake it.

Well, you might consider turning the diff up to normal, then using weapons that strike that balance between keeping you alive, but requiring plenty of hitting to kill. To happily survive as you progress, I recommend letting your main killing skill go up by at least 3 skill ups every time your character levels up; that seems to do well at keeping you on par or ahead of your foes.

Your ideas about giving up Wabbajack and then getting it back after completing the SI sounds very neat! Hopefully that will help eliminate the feeling that you need to level up quickly.