I'm looking into buying a new piccolo, right now, I have a Gemeinhardt 4S, I can't spend a ton of money on one, but I would like to upgrade to a wooden one.
I can spend about $2000 at most.
Has anyone heard anything about the Jupiter diMedici 905ES? That's the piccolo I'm most leaning toward right now.
and suggestions, anyone?

I personally think you should either go to a big flute store like fluteworld and try as many in your budget as you can. I play on a pearl piccolo and you could maybe try that one, because I prefer it over many piccolos of higher prices, like the yamaha ypc-62. You could also purchase a pearl picc and then get a professional headjoint from burkart, or powell perhaps. It's a fairly common practice to do so with flutes, and I think it would also work well on piccolo.

I've tried the diMedici piccolo and liked it a lot. Yes the wood vs metal is a big difference, but I'm not a regular piccolo player.

Their quality was really good as I could tell (for band) although there were some nice ones by Yamaha and Trevor James which I also liked.

Anyway, I ended up with a German Mollenhauer before they were all discontinued and then my fingers grew, so I had to move up to standard C concert flute.

You can always try used ones, so you may end up with a better instrument without paying too much.