Also remember that some ways are impossible to tell apart. 12/10/2008, for example, is 12th October for us in the UK, but 10th December for Americans. There's simply no way to guess at which it is without some context or the user saying which.
What that shows is that while NLP can make systems seem quite intelligent, it's really not a replacement for the user putting some thought into it too. Forms work nicely as they can force input into certain formats. I like NLP, so I always think systems could at least meet a human half way on this.
However, even if we were talking face to face, there's some social expectation you'll try to make some sense (i.e. speak in English). You wouldn't just speak Spanish to me if I hadn't indicated I could speak Spanish. AI-like systems are meant to be intelligent, not psychic -- a point often forgotten by some people.
A dialogue system would help uncertainties since it could ask for clarification (which, frankly, is all we humans do if something's not clear when talking to each other), but if you're talking over email, you really want to get it right the first time as it's not the fastest system.
Again, off the top of my head: I'd say you could make it clear that the subject of the email has to be one of "reminder", "followup" or "todo"... then do some aggressive normalisation on the subject lines that come in (grab a Porter Stemmer or even just take the first 3/4 letters maybe) then force to upper or lower and then check against a massive list of synonyms. Then you simply have to bounce with a help notice if someone really still managed to enter something stupid.
Examples:
Subject: Reminder -> REMINDER -> REM -> matches rule for "REM/EVE/HOL" (Reminder, event, holiday)
Subject: event -> EVENT -> EVE -> matches rule for "REM/EVE/HOL"
Subject: follow-up -> FOLLOW-UP -> FOL -> matches rule for "FOL/REV" (follow-up, review)
That sort of idea. It accounts for RaNDom CapITAlisation, uncertain hyphen-usage and plurals. Make those match rules long enough and you might get error rate pretty low indeed.
I know you've probably already gone over this, but does it really need to be email? Is that the best interface? Is it worth taking a step back (going outside the box, as they say) and working out the most efficient method?