I know this falls more into the Online Logbook category, but a simple Flight Review or Instrument Proficiency check reminder either through email or text would be a cool feature.
Dunno if this will help you, but I set up my calendar in Gmail (Outlook will do the same) to remind me to check my electronic log book to verify my currency dates. More informational for me since I am determined to touch a cloud once a month, but my night currency tends to lapse.
I set up my BFR for of course 2 year reminders (one month before they are due) as the same for my medical.
My aircraft maintenance such as .411 .413 and annual same deal, reminder one month before.
What Allan said is good. I don’t think FlightAware should be used to notify you of something that is your responsibility. There are dozens of calendars out there that can do the same thing and yet not take up bandwidth for more important things on FlightAware.
There’s no need to worry about not getting the notice. I would set it up in Outlook other email reader with a calendar and do a backup in Google and/or Yahoo.
Well Damn…there goes my idea of having FA notify me to make coffee in the morning!!! Or to get up and go pee in the middle of the night!
Dont you just love Fargin Icehole smart-ices like me? 
Uh, don’t be so hasty. You may have something on that last one!