I have a very similar setup to yours. I am having no success syncing with Daylite either. One of the guys here (Sempai) is having success with Daylite so maybe there's hope. He tried to help me himself, but I was unable to figure it all out. I appreciate his time.
Count yourself lucky that you are even getting a response from Pocketmac "support". I posted my first inquiry on 6/29. I received a reply that day. We went back and forth by email until 7/4 and that was the last I heard from them until 7/22. That post was an apology for slow responses and that things would improve. By the end of July, I was pretty steamed so I called their sales line to complain. I got a response from support on 8/2. I tried their suggestions and replied that day. Since then nothing.
LC, did you use a Palm before your BB? Were you using Missing Sync? If so, there may be yours and my problem. I'd rather not uninstall Missing sync, but I may have to. I use it so I can sync Avantgo. I'm keeping my Palm around because I have software on it unavailable on BB.
Here's how I sync my DL info to my BB. I'm sure there's a better way. Automator support for Daylite would help. It would be great if PocketMac worked as advertised. It's one way only. I don't try to make changes on my BB and sync back. I purge all contact and calendar data on my BB. I then export the calendar, then DL contacts as vcards. I then import the vcards into AddressBook and calendar into iCal. Then I sync with PocketMac. The second time you do it you'll need to delete all data from AddressBook and iCal. I know there's an AddressBook sync available in DL, but it didn't work very well for me. Some contacts would have all info, others not. That all cleared up when I exported vcards and imported them into AddressBook. It's tiresome, but it works for me. I do it about once a week or just before I go out of town. So, for me, PocketMac the program isn't completely useless. Not terrible, but close. Their support is another matter.