PDAs forum: Sync possible using Outlook 2000 on WXPto HX2755 WM 2003SE?

Hi,
You may think this is a time warp question, please forgive me. I have just bought an ipaq HX2755 (should have held out for the 4700 with better display) for use as my walking to-do-list, and calendar of all of my families many activities. As I can't afford to upgrade my computer (XP, SP?) and Outlook (currently 2000), can you make any suggestions as to whether I should just attempt to use active sync (on the CD included), or try some other software? I have been reading a lot in this forum on the hx2755, and as I don't care to go online or store contacts, huge files, or many other programs, I hope I have chosen well. I don't plan on entering a lot of data on the handheld, but rather entering it on the computer and just syncing at home, so I can have our schedule with me. As I am older, I just don't want to carry all the lists I have had to generate, that sometimes get lost, or smudged. I wish I had a handheld before now. I read that Google calendar won't sync with older than Outlook 2003, so that idea went by the wayside. I also read that the newer versions of windows mobile, 5 & 6, don't allow you to be as selective about what to sync, or override in case of conflicts. So my 2nd questions is: Would you recommend that I just stay with the current operating system (WM2003SE)? I am sorry the new PDA/handhelds have been joined with phones & GPS now. The phones' screens are just too small for my aging eyes. As for GPS, I have never gotten lost yet, and I have lived in different countries, and many locations in the US, but I do ask directions and can read maps of all types well. Thanks in advance for any advice.
Aging techie.