Physical problem connecting 2nd gen. iPod

I have a 2nd generation iPod from April (or March) 2003 -- yeah, I made my purchase about a month early! Well, it was great for well over five years. But at the end of 2008, I began to have problems getting it to connect. When I would plug in the Firewire cable, the iPod might go into disk mode (and begin charging), but the check mark wouldn't go away. The only way I could get it to connect was to apply pressure to the plug. Then I would have to hold it in until the iPod ejected.
I acquired a new iPod (a "Classic"), so it's not a big deal if I can't resolve the problem the older one is having, but I'm curious and would like to see if the firmware is as up-to-date as it can get and if iTunes 8.1.1 does any better transferring data to the older iPod than it does with the Classic. Just "scientific" experimentation, I guess.
The problem is that I've edited a lot of music since I last synced the old iPod and I don't wish to stand still and hold the firewire plug in that long. And if I let go, the computer will stop seeing it. Is there any way I can gently pull the port back in place? (The sound quality of the headphone jack is iffy, too.)

Kenichi Watanabe wrote:
The problem you describe just sounds like the FireWire port on the iPod is worn out or the soldered connections to the logic board are not fully secure.
One thing you should try is to use another (newer) FireWire 400 cable. There is nothing special about the original thin cable that came with the iPod. So hopefully, the connector that is worn and not connecting properly is on the cable side. Or perhaps a less used cable will connect better with a somewhat worn FireWire connector on the iPod.
If the problem is the connection between the iPod's FireWire port and the logic board, then it will be difficult to repair.
Thank you for your response.
It's not a big deal, as I'm happy with my iPod Classic and the better range of accessories I can use with it, save the fact that iTunes tends to corrupt files as it transfers them. I've already tried two different FireWire cables -- the original, thin, one, and a thicker one -- but while either will charge the iPod and put it into disk mode, neither allows the computer to recognize the iPod unless I press down. I was hoping I could use needle-nose pliers to try to pull the iPod's port back up without damaging the connectors.
(I'm might try it, anyway, considering I don't really need it.)

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