So I'm level 40 with Two Handed, and Heavy Armor resting comfortable at 100

How am I supposed to get to 50, within a reasonable timeframe?

Sneaking around whiterun for 3 hours for 2 levels of sneak, or putting on light armor and letting wolves eat me for 20 minutes doesn't sound too exciting

Any ideas?

Level your smithing, enchanting, and alchemy.

I gained ten levels, alone, just by maxing out Smithing. Of course, at higher levels it becomes more difficult to gain levels.

just play the game man. Do quests, pick up aclhemy stuff, just do whatever. That's the beuty of TES.

This and alchemy. Honestly if you play the game it isn't that hard to level.

try to get other skills up. I think the max level is 80 after you max everything lol.

Put on light armor, and use nearly harmless spells repeatedly on weakish enemies, I suppose.

Basically, you're asking for a way to do tedious grinding without the tedious grinding, so I can't really offer up much by way of solution, other than using your trainers and doing silly things like spamming telekinesis or just letting things gnaw on your shins for a while.

If you haven't done it yet, you can probably use your crafting skills, as well, as if you have the money to buy lots of ingredients at end-game, you should be able to pound through large quantities of the stuff in short order.

Grind other skills. I'm level 52 and my main skills aren't 100 yet. Heck, my one-handed (I DW) is only 48.

ermmm i would say not worrie about your lvl and play the game ??
im sure in the end you will max out your character

Conjuration seems to level up really quickly. Just conjure a sword or something and sheathe it a bunch of times while you walk to whatever place you quest has you go. And i think conjuring things while in combat levels it faster.

No, the things that level me through normal play (Heavy Armor and Two Handed Weapons) are already 100

gaining levels after all your used skills are 100 is just going to be a tedious grind , if you dont want a tedious grind then dont bother or use the console . Each to there own but the top levels wont be achieved without cheating or grinding , theres plenty of levels through normal play isnt that enough?

Pickpocket levels up like mad, I've just been snagging keys arrows and gold off of people as I pass them and I'm already rank 70. Now consider that I've only gone so far as having done all the quests in the immediate area of Whiterun and Riverwood...and by immediate area I mean don't require me to LEAVE said area. Incidentally running into a Bandit Marauder with only 40 one handed and heavy armor hurts like hell. He actually instakilled me with a heavy attack+stagger+finisher because my noncombat orientation has caused everything else to level up in combat alongside me leaving me weak as a kitten.