The only way to restore the missing files would be if you have backups of your email. Otherwise they are gone. As for your iTunes issue, it sounds like you had a bigger problem than just an Outlook crash.
Use a program such as CCleaner to clear all of your temp files. Then try reinstalling the update. You may also consider installing SP3 first.
Use a program such as CCleaner to clear all of your temp files. Then try reinstalling the update. You may also consider installing SP3 first.