I cannot comment as to why you may have lost all speed dial functions but I have had an ongoing problem with Outlook. It does not store either the speed dial or custom ring tones assigned to my contacts. I frequently get sync. error messages regarding a change in my server (which there wasn't) and when I try to correct it the phone loses the speed dial and custom ring settings.
If someone knows where the contact data is stored on the phone I might be able to write a routine that will back it up.
Good luck!
Icer