Your best bet (if you really want an iPod, and won't settle for another brand) is an iPod Video 5/.5G which you will still be able to purchase second-hand relatively easily.
Other than that, wait until the iPod Classic port becomes more usable by the general public.
If you don't specifically want an iPod, you can still buy Sansa Clip(s) new in some places, and possibly the Sansa Fuze if you are lucky.
[St.]