anyone else having iOS5 syncing issues (contacts/iCal)?

Yes, absolutely.

I posted a comment back in November on here.

http://forums.macrumors.com/showthread.php?t=1277507

 

I could be misunderstanding something, but as I read your situation you're trying to have the iphone sync against two sources of contacts, the MBP and iCloud.

The way it's design is to have one source. That can be the MBP or the iCloud. You need to choose which way you want to do it; either have both the MBP (requires Lion 10.7.2 IIRC) and iphone sync contacts/calendars to iCloud or not use iCloud for contacts/calendars. I don't believe you can mix the two unless they're separate sets of contacts & calendar items.

 

Yeah, for best results you want to do one of the these two things:

1. Enable iCloud sync for Calendars and Contacts on BOTH your MBP and iPhone.
2. Disable iCloud sync for Calendars and Contacts for BOTH your MBP and iPhone.

Personally I would recommend iCloud, I see calendar and contact changes propogate to all my devices in seconds. For example, I add a contact in Address Book. By the time I turn on my iPad and open up the contacts app, it's there. Same for iPhone. It's fantastic.

 

Apple calendar is pretty hopeless. I use Calengoo to sync from Google Calendar. Not as nice looking at native Android calendar, but it looks really nice nonetheless.