IPod Shorting Out FM Transmitter(s)??

Hello. I originally posted this on another iPod-oriented forum, and I have to assume that no one has an answer, as it hasn't gotten a single reply yet. Either that, or I don't have enough 'cred' there yet. Nevermind my insecurities, here's the deal:
IPod Vs. FM Transmitter Problem
Hello. My 5th-generation 30GB Video iPod has had some problems in recent months, but none too devastating. It used to require me to 'reset' it everytime I wanted to use it after a prolonged 'power down' period. Recently, however, it seems like it's destroying FM transmitters...or at least not being willing to play nicely with them.
I first had a Monster FM transmitter that worked great for the longest time, then I believe a short occurred in it that would cause the iPod to automatically 'pause' when it would get jarred a little. I gave up on that cord a little over a month ago and got a Kensington transmitter from Amazon. That worked perfectly for about three days and then just abruptly shorted out and completely died.
But it gets better, and by that, I mean worse. I receive the 'exchange' Kensington transmitter yesterday and that shorts out INSTANTLY. I realize that it's entirely possible that I got two defective items from Amazon consecutively, but I have to believe the problem is on the iPod's end. You see, I went out and picked up an iTrip one at Best Buy today, and that seems to cause the iPod to 'freeze' up, the touch wheel barely functioning when it's attached. The iTrip appears to sustain power, though. Unfortunately, I haven't been able to test someone else's iPod with it yet.
My iPod, while connected to my PC, seems to work fine, except that some unknown application is preventing me from ejecting it through iTunes, but whatever. As a standalone device, it also works, and the touch wheel is appropriately responsive. I could be wrong, but I think something happened to it after that Monster cable went on the fritz (even though the resetting nonsense started well before that point). I looked at the USB/power input area, and the 'male' part on the inside almost looks like it's got a tiny char mark on it.
I have the AppleCare Protection Plan, and I'm wondering if the likely scenario is something they'll even assume responsibility for....I've restored the thing twice now since purchase in October '05, having to re-import roughly 5,000 songs after the first time. I don't want to even bother starting that arduous process if this thing is a lemon, if it's going to continue to 'blow up' FM transmitters because of some sort of power surge.
Any concrete information on what's causing this or educated guesses would be greatly appreciated.
I'm about at wit's end with the whole thing, and I'm really concerned that Apple will wash their hands of responsibility. Ever since the 7.0 iTunes update, I've had minor, nagging problems with it, but nothing like the thing potentially being a transmitter mass-murderer.
Sony VAIO Windows XP
Sony VAIO   Windows XP  

Have you reset your ipod? That usually helps with any external devices attaching to it.
I'm also wondering (based upon the transmitters you've used so far) if it's not your car lighter that's causing the short? The itrip doesn't use the charger but the others do and since the itrip is working (albeit slowly) the car lighter might be the source.

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