Problems syncing from contacts to address book

Question

I have an iMac which now runs OSX 10.6.8 and an iPhone 3GS that runs the latest iOS 5.
Long story short, I downgraded from OSX Lion back to OSX 10.6.8 a few months ago.  Got quite a few problems doing so...  ended up creating a brand new user and transferring music, videos and photos manually.  Then, the iOS 5 got out and I upgraded my phone right away.  I couldn't figure out icloud at first but understood yesterday that it works only with Lion.  I thought I'd keep it on my phone if I ever want to install Lion again.
I also realised that I never transfered back in my iMac all my iCal events and Contacts.
So yesterday, I tryied to sync my Contacts, iCal and Notes from my iPhone to my iMac.  In the iTune info tab, under each section, there was a message mentioning that since I use iCloud, I don't need to sync my info through iTune and doing so would possibly create duplicates.  I try to sync them anyway since I only had to in Address Book.  I got the message to merge or replace.  I selected merge (yes I had at least one contact in Address Book).  Nothing happened...  iCal didn't merge anything and neither Address Book.  I tried to create new events in my phone and iMac and these were syncing but not the original ones.  Also added a contact in Address Book and it got sync with my phone.  I didn't try creating one on the phone to sync it through but assumed that it was working.
After going through a few discussion threads, I decided to delete the iCloud account on my phone since I didn't need it and try re-syncing.  The iCloud message in the iTune's info tab was gone so I thought everything would be good and I could select merge my contact again without any problem.  I was wrong...  I lost all my contacts...  I freeeeeeeeaked out !!  Thank God I didn't unplug the phone and restored it right away to get everything back.
I tried it again this afternoon but only tried to sync iCal.  I didn't get to choose between merge and replace and the same thing happened again...  lost everything...  iCal but also Contacts which I find strange because I didn't check the Contact option in iTune....   I got everything restored back even thought it's always scary to try things like this....  So for now on, I don't delete my iCloud info on my Phone and do not sync any other info.  I'm actually scared to plug it in and always double check that my contacts are all there before unplugging.
So here I am...  don't really know what to do...  I read stuff about removing apple.isync files or something...  or other options but they never quite answer my problem...
There is still the option to type all my contacts back in Address Book..  I don't have that many... but it's a pain...
Sorry about the long message here
Thanks for your help and for your time.
Ben

Answer 1

Clearly iSync has got confused about what new data it needs to pull from the phone. Usually resetting the sync history solves this, but as it hasn't for you... try this:
I would suggest sending all the contacts from the phone to the Mac manually via Bluetooth: *Contacts > Options > More > Advanced > Send all Contacts > Via Bluetooth* (or similar, depending on the exact phone model)
This will send vCard(s) which can be imported into the Mac Address Book simply by double-clicking the file that arrives on your Mac.
Merge or remove any duplicates as they are imported. You can also use the *Card > Look for Duplicates* command in Address Book.
Once all your Contacts are exactly as you want them in Address Book do a full backup of them:
*File > Export > Address Book archive...*
Finally, load iSync, click your phones icon and choose *Reset Device...* from the Devices menu.
This will force iSync to remove all the existing contacts from the phone and completely replace them with all the new nicely sorted out ones from the Mac Address Book.
From this point on, iSync should keep track of what needs updating on each subsequent sync.