Here in Ohio, I use a 26 gallon conical, and brew several 20 gallon batches each year, starting right about now when night time temperatures begin to drop into the 30's. I have an attached garage where I can do all my brewing out on the concrete floor where I can sterilize, brew, and clean up everything up afterward with a hose. Once the wort is in the fermenter (on wheels and extensions of course) I push it off to the side, and use a thermostatically controlled electric heater to maintain the garage temperature right where I need it to keep the brew at the proper temperature. Since the garage is attached and well insulated, the temperature never falls below 45 degrees even without the heater, and for most of the year, it doesn't take too much to keep it in the fifties or sixties. It's like having a giant walk in, and my wife likes the added benefit of having a relatively warm car on cold mornings too. Of course, I can't brew that way in the summer, but when you're cranking out 20 gallons at a time, you can brew a year's worth pretty quickly, and if I get in a pinch, I can always do a batch in the basement where it stays pretty cool. I usually put 15 gallons of each batch in a regular half barrel, and the rest in a 5 gallon keg, carbonate them both, and then fill bottles from the 5 gallon keg. I try to drink the kegged beers that taste better "young" first, and let the others age for summer time consumption. This approach is working really well for me right now, but eventually, I plan to build a barn, and when I do, I plan to include a room that I can cool or heat so my brewing won't be limited by the time of year.
I've found that the larger batch sizes are much more forgiving and easier to duplicate, and some of the beers I brew, like my porters, taste really great when they've had a year in the keg to settle and develop character. I'm not knocking bucket brewing, but I just got tired of chasing one batch after another trying to keep beer on hand. It takes the same time to brew 5 gallons as it does to brew 20, and I was spending all my time brewing and not enough time drinking it!
Happy Brewing - Highlander