Recently, I created an item "A Friendly Trade", which is a Mage Hood (0 weight) with a fire shield enchantment. I did it for the sole purpose of swapping it for S'drassa's Tan Hood. I reversed PP'd it, left town, did a bunch of other things. I return to the Guild (days later), and he's still wearing the Tan Hood. I've never done a reverse PP before to swipe an NPC's gear. Did I miss a step? Thanks.

I think the item you trade has to have a higher armor rating than the one you trade it for. Try checking if that's the case.

1) I thought it just had to be higher on the (alphabetized list) and not have a lower armor rating?

2) If that's the case, how can I reverse PP a hood if none of them have armor ratings?

The problem may be that he's already wearing a hood. Does he take it off when he sleeps? If not, he may never have occasion to choose your replacement.

As I was reading this, I was forming the same opinion as glargg. Check and see if he sleeps with the tan hood on. If so, I don't think that technique will work.

also iirc you should always name the enchanted item with some aaas (writing as looks like the word as instead of plural a) you did but thats just to help people who don't know. Why not make a perma bound helm? that might make him take it off. Hmm can you cast bound armor on npcs? I don't think you can but that would work if it did

I don't think he ever takes it off. I tried to reverse PP a bound helm, but I got a "You cannot remove quest items from your inventory". I can't do a custom bound helmet spell on other; I checked that out. I could probably do it if I start the game w/o the unofficial patch, reverse PP, wait for him to switch, PP, then restart the game with the patch. However, who knows how toggling the patch like that might mess up other parts of my save game.

The only reason I want to get this is because my character is a "Shaman" and is wearing Huntsman's gear (vest, pants, mocs). All the other hoods are a little too flashy for that outfit. The only other option I see is to play Shivering Isles. There's a tan hood up for grabs there, as well as a Zealot's hood that looks like it might work, too. However, at this point, I'm level 5, have Azura's star, and have only finished the basic mage's guild quests to get membership (I'm waiting until level 15 to go for the staff). Anyway, I think it might be a tad early to go for the expansion pack, but I've actually never played it before so I don't really know.