Yeah, my all seasons are shot too, and I too put off replacing them to this Spring. Down to 3/32 or so, which although they will pass inspection at, is realistically beyond the safe life of the tire for everyday driving. I remember last Fall, before switching over to the Winters, on rainy days I couldn't comfortably go more than 60 or so without some chatter in the steering wheel from brief hydroplaning. They're fine on dry roads still.
Ordered a new set on Sunday and figuring on getting it in the second half of the week to have them put on.
I typically run my Winters Dec 1st to April 1st on the average year. But it depends on the forecast in late November/early December and then again in March. This year I didn't put them on until the weekend after New Years with the warm December we had. All told I only put 3100 miles on them this year.
I too bet a coworker whether there would be another snow this year. I took yes, he took no. We agreed it had to be at least a steady few minutes of snow, not just flurries, but it didn't have to stick. The stakes are a Friday lunch at a pizza joint we go to. 2 cuts and a drink, or about $7.