Of course technology can improve the experience of driving in winter for most people. And undoubtedly make it safer (for most people). However what you consider stressful, I consider grin-inducing fun. One of the most memorable road trips I've ever undertaken was a 2009 4,000 km late January excursion from my home in Calgary, down through Montana, across Washington state, up into BC at Vancouver and through the mountains and back to Calgary. 17 days. In an S2000. Snow and ice-covered roads all the way. Backroads only wherever possible (including some roads with logging trucks to navigate around). The only casualty was the front clip of the Honda, which suffered a fair bit of road rash, all repairable with a Dr. Colorchip kit. My wife said she found it very relaxing; like motoring through a winter wonderland in a toasty warm sleigh (the S2000 heater is amazingly efficient).
I think getting older affects peoples' perspectives in different ways. In my cars and in my life in general, I'm becoming more increasingly averse to doing things the easy way. Even though I'm in the technology and media business, I appreciate more than ever certain analog experiences, where comfort and ease take a backseat to taking on the challenge myself, doing it the long and difficult way, because there is joy in mastering whatever skill it takes to do it well. Fortunately, my wife is in the same headspace and smiles and goes to the gym when I'm laying hardwood because I can, or swapping O2 sensors on the Cayman because I can, or heading out on country roads together in the dead of winter (we used to use my 911; this winter we will use the Cayman), turning of PSM and sliding around for a couple of hours...because we can, and we think it's fun. Two weeks ago, she did the Jim Russell F2000 3-day racing school at Mont Tremblant in a car with a non-syncro Hewland crashbox. Every other school in North America has moved to sequential boxes, and I convinced here there was merit in learning how to heel-and-toe a Hewland 4-speed. She now is basking in the glow of mastering an admittedly outdated driving skill that only a few old-timers on this board could appreciate.
There is now an entire generation that believes AWD is a necessity for winter driving, and would have no clue how to power slide a car in a controlled fashion through an icy corner. I believe - even in an age of electronic controls that admittedly work extremely well - that these are useful skills for an automotive enthusiast to possess, and applying them at times in a safe and effective manner contributes to making one a better driver than someone who always relies on technology. (FWIW, if I had a 75-mile daily commute on an icy highway I'd leave all the nannies on...then deactivate them once I hit some icy/snowy side streets where there was fun to be had.)