I have tried "de-soldering" a couple of headers before and it isn't very easy, I have had no luck in succesfully getting one off. (I have soldered about 40 of the things on, they go on easy but come off hard)
Drivers are out there for Win2K for about everything except for the touch screen BUT the latest posted driver may work but I haven't tried it myself. You will want to add a 256mb sodimm for better speed, get the 16 chip design one. I have loaded Win2K on a GCT and it really isn't too bad, it's better than Win98 or WinME.
Do a search on RS232 here in the GCT section and you will find my thread on using the Badflash RS232 board to convert the TTL com ports to RS232. The i-Opener RS232 board is the same pin on COM1 (modem) port but the board is a little too long and you can't get the board in due to the USB and Phone lin ports. In that thread I made an extension cable to go to the COM1 port to the board and with the help of Programmer made a connecting cable for the correct pinouts for the COM2 port. I used one GCT as a EMU computer when the H card lived! it worked great; it booted to MSDOS on the compact flash card and ran SLE perfectly!
Drop me an email, I can send you a IDE header for $6 PayPal