Quote:

It's one of these fifth generation ipod.



I guess it depends what having it working as new is worth to you. Check out these guys; I believe they are in your neck of the woods (Toronto area), and can replace the damaged audio jack with a new one. Haven't used them myself yet, but seen them mentioned in several articles; they are supposed to be reliable.

I would prefer a like-new fully-working iPod versus one with a widget permanently attached; $50 would be worth it to me.

That particular model (5th generation, video) is also very hackable -- you can install the RockBox firmware on it for extra features, etc.