I think you have to be more specific about Chibi's items. She really actually set the forefront for quality items on this site though so I'd assume that they would all be pretty safe.
But yeah, I have a lot of items that could possibly be changed.
Yeah. But you haven't purchased all 27 of those outfits yet so you're lucky. There are others who spent a lot of time working on an avatar and then questing for the items they used in them only to have their avatar change into something completely different and have it all have been a waste of time and gold.
No. Jelly sees me enough to know what I'm wearing and when. So I don't really bother going into Admin's Pick. And besides, I hate seeing all the people ask "Is this good enough for admin's pick" and it being a total newb avatar and other people saying "yes you should go for it!!!" when they know it's not good. I'm not saying that they should say no, but I think they should tell them to work harder on their outfits rather than giving them false hopes of winning that week.