I have not tried syncing with Win7 yet, so that the following info for what is
it worth (not much!) but generally, most sync problems have the same few
issues. First, can you tell what is syncing when it hangs? (Contacts,
Calendar, Favorites, etc.) If so, turn that item off and try to complete a
sync. Then you can turn it on afterwards and see if it hangs again.
For the item type that is hanging, the problem is usually one specific item
the device does not like, because it has corrupted information or simply
information the device cannot handle- like in a Contact or Calendar's "Notes"
field, for example. (I know WinMo has issues with long notes fields, or
certain objects embedded in the notes field.)
You could try ScanPST (or Detect and Repair, or whatever your version of
Outlook calls it) and see if any errors are detected and repaired then try
syncing again. Maybe something went awry with your Outlook PST when you
upgraded to 7.
Assuming that accomplishes nothing, the next thing to do is "divide and
conquer." Take the entire contents of the problem item type's folder and
move (cut and paste) all the items to a subfolder (the WinMo device cannot
from the device because they were "deleted" from the PC (from the device's
point of view, they were!)
Now, grab the items a few (or bunch) at a time purposefully (e.g. for
Contacts, maybe the As, Bs, Cs and Ds, then the Es, Fs, Gs, and Hs, etc.)
and copy them (rather than cut/paste- let us keep an entire record of that
item type "just in case"!) back to the main folder with the device connected
so it syncs them as you move them. Wait for each batch to finish syncing
before dragging the next back to the main folder. Eventually you will find a
batch of them that "hangs" while syncing. When you do, remove them and
bring that batch back in smaller batches (e.g. just the Fs, then just the
Gs, etc.) and repeat until the find the sole item that causes the sync to
hang. Recreate a new entry of the hanging item manually, save it, let it
sync, then continue copying in batches for the rest of the items (in case
multiple items are causing problems.)
[You'd think after ten years Activesync/WMDC could just pop up an error
saying "Can't sync 'Smith, John' Retry/Cancel?" but instead it just grinds
away or fails when an error is encountered!]
Hopefully this helps, or at least helps find the problem.
Good luck!