I did try rebooting the Laptop and for the first time it did upload to about 75% before it finally failed, so you are on the right track, but there is definitely a problem with running the editor software on the Dell D610 running XP Pro. I tried doing an upload with an older Dell Inspirion 7000 running Win 98 and it uploaded first time.

I may have to consider trying a USB to Serial Port or PCMCIA to Serial Converter just to see if it works more reliably.