My company is upgrading my 8830 to a Storm2. I am currently running DM 4.6, will it work to run the device switch wizard on a BB running OS 5? Do I need to upgrade to DM 5 before making the switch, or does it really not matter?

It doesn't matter what version of DM you use.

However some of the applications installed on your 8830 may not be compatible with your 9550.

Thanks, I assume that I'll have to reload all the apps, but I'm not really a heavy app user (not much available for the 8830 anyway) so it's a minor inconvenience.

No, it will carry over apps, the point being, some that you may have might just not work on the 9550.

This is actually a good thing, not transferring apps. This was a HUGE problem for me back in my days using Treo smartphones. Just upgrading from a Treo 600 to a 650 and using the old apps caused all kinds of havoc. Best to start again, with fresh downloads designed specifically for your new model.