Just got a 32 gig off some guy in BFE on CL for 340.

I'm selling my jailbroken 16 on CL to a fellow today for 300.
I went from a 80 gig 5.5 video to a 16 gig, and there is no comparison between the two. The interface for playing music, etc., can't be beat. It's incredibly cool to have email and the web at your fingertips, and the touch works as a credible pda/scheduler. It's small, light, and is not as fragile as the hard drive based pods. Unlike my photo or 5.5, I havent' had to take one back to the apple store yet. I thought I'd miss the storage going from 80 gigs to 16, but I haven't; I've learned to manage my music and videos better.
Jailbreaking the touch raises it to a whole new level of awesomeness. (I'm forty, and don't like that word being overused, but nothing else adequately describes it.) There is a wealth of 3rd party apps being written for the platform every day, and they exponentially increase the usefulness of the device. You wouldn't believe how much attention they get, even from my iPhone toting bretheren.
As for your question of, 'Gee, what if they bring out a new device?', I say to get one now if you can find one for a decent price. I'm not being paid to plug craigslist, but try looking there if you live near a large metro area. Let's say they come out with new software in June or July. Guess what, you can buy the upgrade! I know a lot of people were made over the $20 functionality charge, but it sure beats having to buy a whole new ipod for some cool new features. They may come out with new hardware (3g, better camera, or whatever) but I'd be willing to bet that the non software features will come out on the iPhone first, and on the touch six months or so later. And if they come out with a feature you can't live without on a new model, you can sell your current rig as long as you protect it and take care of it. More than likely, they'll just upgrade the memory and hopefully the same price points.
I don't know what Steve will come up with in June, but I'm having a hard time fathoming what he could pull out of his pocket that would make me throw down my current jailbroken touch in disgust.