There seems to be 3 general categories of gear in Skyrim: Heavy Armor, Light Armor, and Clothing. These seem to (roughly) correspond with the three class archetypes of warrior, thief, and mage.
In Elder Scrolls games, finishing quests to get rare artifacts is generally a good way to get uber-powerful equipment. Another very effective way is to enchant armor and weapons yourself, and as a bonus you generally don't need to leave town for more than a few materials. In Skyrim, crafting your own now seems to be a very viable option.
What is the most powerful (by AR or damage) user-crafted gear, and how would one obtain it? I assume crafting skill bonuses would be required for smithing and enchanting; how would you attain these bonuses?