Okay, I may be way out of left field on this, or maybe everyone but me knows about this site but me, but I just found COZI, the god of calendars. I hate google calendars, because they aren't very user friendly in my opinion, but this one?!? OH DEAR GOD, I'm in love. Instead of members of the family, I set it up by community I'm in (with an extra group for PSL/un-homed characters), and I started filling in birthdays and anniversaries, figuring I would use it sometimes for that. Then New Years rolled around and a few friends all decided we'd try to go all year without getting nudges or warnings on our communities...
I literally went in and put when I'm updating everyone. Set it to repeat on the same day each month, and I get a friendly little reminder e-mail with each week (INCLUDING COLOR CODED COMMUNITY NOTATION) and who needs updated that week and on which day on it. Because I'm OCD, I set up to print by the week, and now I can check off each one as I get done.
I'm gushing! I know. Maybe this isn't as much fun for anyone else, but this thing just saved my RP sanity. Now I won't wake up on a Wednesday with three nudges and have to run to come up with ideas for three different characters! Now I'll never forget character's birthdays! Or their SO/kids' birthdays!
So, yes. Cozi. The god of calendars. I'm shutting up now. :D