The Outlook client is not the issue. Once purchased you can continue to use it for 10 years if you like with no further licensing or other costs. It's the Exchange server itself that legally requires the CALS for every new version of Exchange.
As far as Microsoft Server vs Linux Server for mail well back in the day it was Linux but Exchange has pretty much taken over that market now for a long time and handles the job just fine (again I'm only dissatisfied with costs, not the product).

Providing further details probably has little bearing as well as most companies use Exchange very similar. Yes sharing of calendars, forwarding to multiple contacts, different scenarios for delay or redirecting mail, public folders, etc.

If someone has actually made the switch then they would be familiar with what worked for them and what product they settled on.

To answer your question though - current user base at 500 with email accounts. About another 300 accounts without email. About 50 accounts that have mail enabled contacts but not a mailbox. Business is growing and these repetitive costs are quite a drain. Money spent over and over on licensing could be used on other projects if it was made available. But so far not sure - if no one has done it that's okay. I will probably at least dive in and take a look and see what I come up with. Just have to find some time to do it....