Editing Documents Offline within Outlook

I am currently looking at using Outlook 2007 for our mobile users to
be able to work when away from the office. If they check out the
document and then edit the offline (Outlook) version whilst out of the
office, the changes are automatically synced when they send/receive
within Outlook. If they then check-in the document, they can add their
comments to keep version history.

The problem that I (and the users) are finding is when the document is
NOT checked out.
Say they are out of office and realise they forgot to check out the
doc they are working on. The document is still within Outlook so they
can begin modifying it. When they arive back in the office and try to
sync, it does not do so automatically (because it's not checked out).
I open the edited document within Outlook and then use the 'Update'
option and the error about the file being read-only is shown (again,
because it's not checked out).
The next step is to check out the document, hoping it would work this
time. The only problem is I checkout and this server copy overwrites
my local copy.

Anyone know of a workaround, because we want both the 'Forced' check
out feature and the Outlook offline capability.

Regards,

Dietmar
.