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As an aside: You can say "skills level up", but this has nothing to do with the character or monster level.
Once I leave sewers: Arena (including side quest for grand champ) Fighters Guild > Mage's Guild > DarkBrotherHood and finally Thieves Guild. Obviously any random side quests are completed along the way. I only really start the main quest when there's little left as I hate roaming around with Oblivion Gates everywhere and they're tedious.
I tend to leave DB and Thieves till last as you'll be doing alot of sneaking / stealthy type missions and by the late stages, my stats, especially sneak and magic are sufficient. I want to enjoy sneaking around without hearing "WHO'S THERE!" everytime I move a step -although hilarious to listen to. Also by completing MG before TG is of an advantage as there will be a quest in TG, to 'acquire' something and there is extra internal dialogue which makes me chuckle.
As an aside: You just repeated yourself but said it in different ways 3 times aka you just wrote me a nothing burger. You can always choose to not level up your character or Idk...use enchanted items, poisons, and custom spells, or even better is to lower the difficulty slider if it gets too tough.