I held off on upgrading from Entourage 2004, but finally gave it another go with new service pack 2.
Right away, I notice that emptying deleted item makes program crash. So I'm back to 2004. Any opinions on 2011? thanks

"avoid using office for mail"?

Well I'm comfortable with it after 7+ years.

It would appear you're not alone in having problems with Outlook 2011. This is part of a note from a MacWorld Weekly bulletin I receive:

"Reader Charles Dane has entered a hellish loop of Microsoft's design. He writes: "I installed the latest Office 2011 update and now I can't open Outlook. When I try I'm told that I must update my Office database. I do that and some tool appears that updates my identity. When it completes I'm then told that there's a problem with the Office database and I have to rebuild it. Okay, so I do that and then I'm told that my identity is older than the version of Outlook that I'm now using. The solution is to launch Outlook to rebuild the identity, but when i do that, the loop starts over. Help!"

I'm afraid you're not alone. I encountered the same problem as I'm sure many others did (particularly given that Microsoft issued a support document that outlines every inconvenient step you must take to make Outlook usable again.
- Christopher Breen"

Yes, Microsoft stepped in it, as can happen, and meanwhile has pulled the flawed updater. It will undoubtedly issue a patched updater soon. But you only quoted the part of the MacWorld article that mentioned others had experienced the problem, and omitted the workaround for the problem provided. Read that here: Undoing the damage wrought by Microsoft's Outlook update.

Whether or not this episode should argue in favor of switching to another email client I'll leave to others to discuss.

My issue was different. I 'm in the group that Outlook was crashing when trying to deleting 10 or more message out of the deleted items folder. I'm back in safe Entourage 2004 until I hear some news....

No discussion ... just switch to Thunderbird.

Email is so complex, no energy to learn a new client, but thanks.

It took me ca 5 minutes to set up 3 email accounts on different servers (both IMAP and POP3 accounts) on Thunderbird.
Bottom line: Work in all with the same 'template'.

I don't know if this is going to help with the Outlook problems discussed in this thread, but the latest update seems to address several:

Description of the Microsoft Office for Mac 2011 14.2.1 update