My individual preference is to brew 10-gal batches, winter, spring, summer, fall. However I'm lucky enough that there are enough +32F days in winter to wait for one to do what I prefer which is to brew on my covered patio outside. This way my hoses don't freeze solid, and when I chill with an IC the runoff doesn't turn to ice before it evaporates (usually).
To each his own, but I recognize that it is much more challenging in a more northern/frigid climate, and in that event I would try to adapt by brewing in a garage, even if I needed a space heater and a fan. Water runoff would seem to pose the biggest problem, so as not to create a skating rink on the lawn and/or driveway.