Cameron,
I work for Ipswitch Imail Tech Support. What I can tell your right off is that you are running a VERY old version of Imail. We just released version 11, and it has a lot of the same functionality as Exchange. You can share calendars and contacts from Outlook and/or webmail, externally or internally, and now has the ability to do mobile sync of these items to smart phones. If you are interested, I can help you install a trial version of 11 and you can give it a test run to check it out.
The number to sales is (877) 488-7341
The number to tech support is (706) 312-3550.
I PMed your my email address.
Please let me know what I can do to help get you started,
Danny