What do you find more tolerable? (averages, town, season, humidity)
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lets say you wake up in the morning and want to take a quick drive down to the shops to buy a few things and some beer.
In 90F, this would be a very simple task, simply slap on a shirt and shorts (takes all of 1 minute), grab ya keys and start ya car up.
In 0F, you will have to find appropriate clothing and then layer them on. Then you try to start your car, but the bloody thing won't turn over. After 5 tries, you get her started, but have to wait 5 minutes for the engine to warm up. You might then have to shovel a crapload of snow out of the way. If you have steep icy driveway, then good luck with that ****, it's another several minutes to apply the snow chains (or winter tires, which is another chore that is unnecessary in the 90F scenario). Then you deal with icy roads, maintaining a low speed and a sharp, nervous grip on the wheel just incase you hit a patch of ice, and there is the chance that there will be unplowed roads and/or parking spots on the way/at your destination. If you do make it to the shops, you then have to peel off all your layers as the temp inside is comparatively boiling. Once you checkout, it's back on with the layers, hoping your car will start then slowly struggling home to avoid skidding on the invisible ice patches.
Why are we talking about 0F? The OP said below freezing, that's below 32F which is pretty mild, 0F is a whole different story. If it's winter, your house is probably going to be somewhat cool, so you'll already be wearing a sweater, pants and socks. All you need to do is put on some shoes, and personally I'd just grab a coat, not bother zipping it up or getting hats and gloves. Even if you find that insufficient, you can zip up and put on gloves and maybe a hat in about 10seconds as you're walking to the car. Stores tend to be pretty cool, so you don't need to remove your coat especially if it's already unzipped. At 32F, salt/sand +sunlight will do a pretty good job at keeping the roads clear of snow and ice and winter tires can handle snow pretty well and your car should have no trouble starting.
Meanwhile at 90F, stores often put the A/C ridiculously high and you'll likely feel cold in shorts and t-shirts. If you left your car out in the Sun it'll feel like an oven and the steering wheel, seatbelt and seat (esp if black leather) will be burning hot.
Honestly though, I don't consider either to be a terribly big deal. I can break a sweat in a sweater if it's 10F and doing intense physical activity like shovelling snow. When I was walking to university in -40F windchills my upper body was getting hot with 4 layers (t-shirt, shirt, sweater tucked in plus winter coat).
At the same time, 90F is not too bad if you're not doing intense physical activity. I've gone on long bike rides in 85F (at a leisurely pace though). I guess I would prefer 32F but mostly because my house has heating but no A/C.
I didn't depict anything, that was BBQ King, but I'll share my experience from yesterday when it was 0F. Following the already absurd 10 minutes to scrape and rid the car's surface of ice and snow, I had to try 7 times to get the engine to start because it was too cold. After spending another 7 or 8 minutes allowing the motor to warm up sufficiently, I figured it was finally business as usual. I pulled out of my driveway and the car began making loud grinding and squeaking noises I had never heard before. That doesn't strike me as "running fine", but whatever you're the expert. When there was enough of a clearing I started to pull out of my neighborhood onto the main road. But instead, when I pressed on the gas I went nowhere because the back right tire was spinning in place in the slush. By the time my car finally started to slide free and onto the road, there were more cars coming and I had to abruptly stop again to avoid skidding in front of a semi truck.
P.S. It's important to note that since I don't have a state of the art BMW with traction control kept in a garage overnight, that means I made all of this up.
Sounds like you need a better car, not a warmer climate.
PS It need not be expensive. Mine is seven years old and has 100k+ on the odometer and it has run just fine in this harsh Minnesota weather.
As much as I hate heat I hate freezing temperatures even more, so I'd take the 90 degree highs any day, so long as it's a dry heat. If it's 90 and humid I'd want to die in either situation.
Below freezing or above 90F weather? For daily highs, I mean.
A daily high below freezing? I even prefer a +90F day over a day with a low below freezing, but a high? Damnit that has to be the worst experience ever.
90F is easily far easier to manage than a daytime temperature below freezing. Now, if you're talking 90F with 100 percent humidity or something like that, maybe we can debate.
I'll take scorching hot over cold any day. I love extreme weather, always have. I live in Boston, and loved the winter a couple of years ago when we had copious amounts of snow and frigid weather. But thanks to Raynauds, that puts a damper on my enjoyment of cold. I won't move south because of Raynauds, but I just wish my hands wouldn't always go numb no matter how much I protect and warm them in the cold.
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below freezing definitely, cuz you can get to snugglin and freaky lub makin by duh fire with chestnuts and cocoa and SH**... 
