I used to sit out on my porch to smoke during the winter, regardless of the weather, unless it got below about 20ºF. But the circulation in my feet is not as happy as it used to be. After some nasty frostbite on the tip of one toe a few years ago, I decided that when the temp is below 40º, I would go inside. That does not include physical activity. It's just sitting on the porch with a computer on my lap that is a problem.
I've adopted some unorthodox methods of maintaining my pipes. Immediately after finishing a bowl of tobacco, and dumping the ash, I forcefully blow through the bit, while holding the pipe over a wastebasket (to catch any crud). Then I mop the bottom of the bowl with a Q-tip. This minimizes the accumulation of goo, and reduces the need for pipe cleaners. I buy 12" craft pipe cleaners from Walmart. (They're made of some synthetic fiber, but that has caused no problem over years of using them. And pulling 12" of cleaner through a bit really gets it clean.) I also have a steel rod roughly the diameter of the smoke hole, for clearing it when it gets clogged. I also have a very thin steel rod that I use for removing gooey bits from the smoke hole opening in the bowl.
I use the flattened end of a cheap pipe nail to keep carbon buildup under control, occasionally supplemented with my penknife. Some of my pipes date back to the early 1970s, and are still in prime condition. I even have a Missouri Meerschaum from 1971. When the bottom finally burned through, I spackled it with epoxy, and it's been happy ever since.
So pipes and pipe tobacco blending are mostly a winter thing for me. A cigar requires so much less fussing, and no cleaning. But a cigar makes the house stink, so I won't smoke them indoors. (The smell of pipe tobacco in my study just reminds me of what university libraries used to smell like, back in the tobacco-friendly days.)
Bob