Had the same problem with Money 2006. Don't think that Money syncs yet properly with WM5 & AS 4.1. The only one that I found that works is Cash Organizer
http://www.inesoft.com (and even that isn't perfect). While it will sync eventually, I have to unplug and replug my PPC in every other time to get a connection without a Cash Manager communication error message. It's a pain but at least it works consistently (half the time

). This, of course, may only be my issue - your results may vary.
SPB Pocket Finance is also supposed to work but I never was able to use it successfully. It took literally 18 hours to sync the one time out of 50 I finally got it to work. Both have trial versions, so back up your Money file and give them both a go to see what works for you.
Hopefully, someone from Microsoft is aware and working on it. Honestly haven't heard a peep other than the original scattered reports of it not working.
db