I think people would want to have things "oversimplified" -- one of the biggest barriers is probably not wanting to research / figure out how to set up for commuting in the winter. Another added bonus is "buying into" the winter commuting. If someone spends the money on the package, and there is a whole group of people for "positive peer pressure," that person will more likely commute at least some of the time during the winter.
A workshop on setting up bike and self for winter commuting would also be good. That way people could get standard information efficiently, decide whether to buy the package, and get any questions answered.
Biggest concerns for me: mechanical failures, especially (canti) brakes icing over. Best setup for bike for different weather conditions (skinny tires vs. studded tires for one). Whether to ditch rear derailleur (I don't have a front one) -- internal hub, fixed gear, or single speed -- leaning towards fixed gear which can also help with brake problems. Alternate means of getting home if weather is too bad to ride back home, or if there is an emergency. (Here we can get a couple emergency coupons for a taxi, bus, or light rail every six months.) Keeping batteries charged in cold weather. Lowest temperature / worst weather I can reasonably commute in with my current gear (hoping for 0F, medium snow, moderately heavy rain).




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