Honestly, the only thing you have to keep in mind when running a soft top in the winter, is never ever never ever ever try to remove ice and snow from it. Well, you can lightly brush off the snow, but don't force anything. As the top warms up (sun, heater, weather) it will clean itself. Never touch the side/back windows because they will scratch.Yeah--my first Wrangler came with dual tops and my current Wrangler is only hard top, so I've run hard tops in the winter.
I know people in the north run soft tops, but I can't find good info on how to deal with ice on the rear window or if it's even an issue. I appreciate the shoutouts--I'll follow up with @stil2low if they don't reply to this thread.
I should have added this: I'm in way, way upstate New York in the Adirondacks. North of most of the population of Ontario. I can see the lights of Montreal's suburbs on my drive home in the winter.
I have no issues with staying warm. Personally, every Jeep (TJ, JKU, JL) I've owned has had an awesome heater. I have been known to drive topless in 45 degree weather with the heat blasting
Just make sure that everything is buttoned up. Windows are in properly and snug. Then you really should be fine.