When I plug my my Ipod classic into my PC it crashes

Because of the bossy media player conflicts that go along with Itunes, I decided to use a different Media Management software component in my Windows Media Center Edition PC( Sony Vaio ). I have almost 85GB of music on my Ipod Classic and it was quite a laborous task to actually sync all of it w Itunes at first, but Media Monkey works great. Anyway, now after successfully using this to add music from time to time with no difficulty, now every time I plug the Ipod classic into the machine, it recognizes it like always, but quickly Media Monkey stops responding.
   ..............wait there is more, I tried just for kicks plugging in my old scratched up class action suit 2GB Nano, and BLAM!  No problems.
So, I'm sure it could be Media Monkey also, but every time the Ipod classic is plugged into the USB port, before MM can get going, the "safely remove hardware" icon appears in the tray, and then MM stops responding.
........Whenever I click on the Safely remove hardware icon, a tree shows this
                                                                                                USB Mass Storage device in Drive:D
                                                                                                          Apple Ipod device
                                                                                                                  then my HP 2400 series printer DOT4USB .....kinda like this!  
               P.S. I used to have an Iphone 3GS and Itunes kept poking my eyes out. However with the Iphone, I was forced to manage it w Itunes, and last year, it started throwing up a WARNING box when I started up Itunes, telling me that my CD/DVD burning drivers were missing..."please reinstall Itunes". I must have actually tried 3 or 4 different versions of the **** Itunes software because it never stopped giving the WARNING...I Hate You box every time it started up.
Nevertheless, I can live without Itunes, because I assassinated my Iphone. However, I just want harmony. HELP ME PLEASE! I understand that my PC is a strange species, but I can't stomach ging up XP, and learning all the BS over again with a differnt OS.  

Many thanks for the reply The Hatter!
The machine isn't new but is new to me, I formatted it and re-installed OS 10.5.8 and installed latest updates. Spec is as follows;
MacPro3,1
2x Quad 2.8 Xeon's
2GB Ram
ATI Radeon HD2600
I'm running the display through the analog cable into a converter. There is HDMI port but I guess to try that I'd need to buy another type of converter (if one exists). The display doesn't have a DVI port so maybe this is the issue? Lower resolution settings in OS fill the screen nicely but obviously this looks totally waff as its all big and low res...
Looked for an update on the ATI site for a newer driver but my machine says it doesn't need updating.
I wondered if there might be some software around that can give me more options in OS for display settings?
Not the end of the world but its very frustrating that I've lost 4 inches of my display for no obvious reason!

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