I've been tossing around the idea of starting a group of people who are committed to buying Bitcoin every month. Can be a small portion, like 5$, or however much people can afford (I suppose it would make sense to use higher amounts for fee reasons, though). I myself have set up a monthly wire transfer from my bank account to Coinbase and a recurring purchase of Bitcoin every 1st day of the month. This is really simple, and you keep investing and $-cost-averaging your BTC purchases.
Who's in?
Good idea. I wouldn't mind buying regularly though. By regularly I mean buying when Bitcoin is down and selling some/all (if you want to) when it's up.
I believe this can be done automatically now as I have seen few members promoting services like that here