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If you have a backup program that runs, be sure it's backing up your outlook .pst file. That's where all the outlook contacts, email etc. is stored.

I know you said you tried Outlook in the past but I'd strongly recomend it for a couple of reasons. One is that it's as main steam a you can get for a business class email program. So, anything you learn with it translates to just about any company you walk into. It also means there is a wide base of people to get help from. It also supports setting up multiple email accounts within the same program. The contact book is good and the calendar featurs are good. Much of it's functionality comes with being in a corporate environment but it's still strong as a persoanl email client.

I'd say invest the time in Outlook. Many people will point to other things and there will be a feature here or there that's better but, this is the defacto standard in companies.