Okay, this crap just cost me an hour and a half
So, I thought I'd share the short answer with the rest of the class...
Q. Office 2010 Professional Plus was installed on a Windows 7 system (mine) that previously had Office 2003 Professional. I set the options in Outlook for Always Check Spelling Before Sending, but the only corrections done were capitalizing first letter in a sentence and days of the week. No misspelled words are corrected automatically or even manually in either Word or Outlook. A manual spell check always finds no errors. Miscellaneous (Google) suggested repairs tried to no avail, so...
How can I activate the broken spell checker?
A. In the registry there is a folder named "override" (that shouldn't be there). Deleted it (make a backup first if you like) from the registry and now everything works just fine.
Here's the culprit:
HKEY_CURRENT_USER\Software\Microsoft\Shared Tools\Proofing Tools\1.0\Override
So moral is: Crash the Override and life is good(er)