Put both your cars up for sale, at a price where someone might bite, while at the same time it would be a no-brainer to sell the car. Market it well. Use proper language and complete sentences in your advertisement. I did exactly this, and the world decided that I no longer needed my truck.
My example was that my first child had just arrived. My truck was a 2003 single cab tacoma pickup (the fuel efficient one). This truck was fantastic when it was just my wife and I. Does not work for a car seat, so it became the "other" car. I put it up for sale on Craigslist, extolling its virtues, frugality, and uniqueness. I pointed out the ways it had been cared for, and why it was different. My asking price was at least $1000 over market rate, and it sold for my asking price.
My current car was one that was too cheap not to buy, although it came a year later. It does have newer safety features. I got it for cheap because it needed some mechanicals, was high mileage, and cosmetically beat to hell.
So, my advice would be to list both cars for sale. At the same time make a list of newer vehicles that have the safety and driver aids you want. Look diligently, and find one that is rough. By your descriptions, a car with plenty of new driver "apprentice marks" on the bodywork would be ideal, and bring the price down a lot. Also look for cars that are not popular now, or have taken hard depreciation. Older hybrids are cheap now, with cheap gas and paranoia of their complexity. Volvos depreciate like mad, I think because their demographic wants newest/best. Used minivans have outstanding depreciation.
And for chris-sake, buy some studded snow tires or Bridgestone Blizzaks for both vehicles for next winter. The net price is the cost of switching the wheels/tires twice a year; since wear is now spread out across 2 sets of tires. The first accident they avoid pays for the capital investment, by not having to pay that insurance deductible. Tires are just about the most important factor in avoiding a wreck, and I would take a 1987 rwd sportscar on new snow tires over an AWD 2010 on all seasons in a blizzard. You can avoid the price of tire mounting yearly by getting some spare wheels off of Craigslist or the junk yard, about $100 for the set on each car.
