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How much of a pain is it to try the 60 day BES trial and go back to the web client after - I.E: do we have a bunch of re-configuring on the handhelds.
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If you apply IT Policy (a feature of BES similar to Group Policy in windows) make sure to keep the Default policy intact--with no settings. Create a separate policy to push your settings. If you end up going back to BES and want to restore policy to its default state, you'll want to change all the BBs that have activated to use the Default policy. Otherwise you won't have an (easy) way to put them back as they were.
Our experience with BIS (and Desktop Manager, for that matter) is that it's very high-maintenance compared to BES. I can't imagine my client ever dropping back to BIS. Like all middleware, BES was heinous to set up, and we were hit hard by some of its memory leaks, in particular, (all now seem to be fixed or worked around) but now that it's up & stable, it doesn't take much of my time any more.