My first thoughts would be whether you do really need roaming profiles; as
you've discovered they are a major source of headaches, therefore I would
only implement them if there is no workable alternative. It isn't just the
setup either, it's the ongoing maintenance-costs owing to problems being much
more difficult to diagnose. Furthermore, I've yet to see a setup where
Outlook (non-express) works acceptably with roaming profiles, UNLESS it's
working in Exchange-client mode as opposed to POP3 mode.
If you don't want to go the Exchange route, then Thunderbird offers an
alternative email platform which is fully network-compatible, that is, a
user's email AND settings can be stored in a home-folder on the server, so a
user sees the right email whichever machine they use. Provided the home
folder is accessed as a drive-mapping, this does not neeed roaming profiles.
Whether you need roaming profiles depends on whether you need users' own
settings and cusomisations to migrate between computers; if not, then you
probably don't. As for the data, if the setup is server-centric then users
should be storing their data on the server anyway, in which case there is no
need for "My Documents" to be downloaded each time a user logs-on.
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