Ny penalty to wearing stolen items

a quick way to see what items you have equipped would be to set all of those items to favorites. then all of your equipped items would show in that menu.

there are only these item slots: head, armor, gauntlets, boots, 1 amulet, 1 ring, two hands, 1 shout/ racial power.

enchantments can vary greatly, so the item comparison only takes the base damage/ armor into consideration.

you should be able to equip any item as long as you have that slot free

Yes you can. When you sell the stolen goods to a fence, or a merchant if you have the perk, and repurchase it, it will no longer be stolen.

There are some items that retain the stolen flag, such as unique items from the Falmar museum.