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I find it very very funny that Miele is considered expensive yuppie stuff in the US. Here in Denmark they are among the more expensive ones, but about as unstylish as possible, it's what the farmers buy when they have earned enough money. Oh and every slum laundromat uses Miele equipment.
Your proposed once per day automatic check-in of everything is a nice idea for a group such as your ArsDigita companay with it's fairly non standard mission statement.
In more mundane companies however you usually have at least one mid-lewel manager who will see the amount of code checked-in every day as a measurement of individual emplye efficiency, and wrech all sorts of havoc with this misguided "knowledge".
I'm sure some of you have expierenced mid-level managers who were too dump to even figure out how to do this, but I have never been that unlucky ;-)
Apart from this your proposed method sounds remarkely similar to what I have been doing for various db backed websites over the last few years. It has proven itself to me to be a great time saver and I don't even want to calculate how many near disasters with their associated all night fix-up sessions it has saved me or my co-workers from.