I have given up on using this software. Missing Sync for Palm used to work better than this. Maybe it's google's requirements, who knows, but this simply does not work. I've tried SyncMate, which is somewhat better, but gave up on that, too.
Just give in and sync with google in the cloud. In the long run (and short run) it's just easier and more reliable. Get a google email address, even if you don't plan on using it. And if you don't, why did you buy an android phone, anyway? Best of all, it's all free.
Contacts: there is a preference setting in Address Book to sync to google (and yahoo). You may have to do recursive syncs and merge contacts a couple of times to make them them same. Be sure to back up your contacts first.
Calendar: ditto. Back up your calendar! Sync TO goggle calendars and then subscribe in your android system. You'll have an iCal copy and google copy, so configuring it is kind of a pain. But when you do it once and have it right, you don't have to mess with it any more and it syncs without intervention on your part.
Files: dropbox, dropbox, dropbox.