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hippy
ugosantalucia
Do you want to do it all outdoors? I think these days indoor is accepted too.
Obviously the only real way of doing it is all outdoors and in a place where there is some sort of winter (short days, cold... you know what I mean).
You can break it down to 40 miles a day including the 25th and it's not too daunting, but realistically there might be a couple of days when you can't ride for various reasons (ice, booze?).
My advice is keep an eye on the weather forecast and ride accordingly. If a good day is on the cards, make the most of it by doing a longer one, if it's wet or dangerous, see what you can do when it's safe to ride.
I have stop doing it when they stopped giving out the cloth roundel... I kind of liked receiving it in the post, feels a bit like a trophy at the club awards night... without that carrot, I really don't feel the urge to complete a particular set distance, so I don't even enter it anymore.