Don't quite understand the reasoning there. Figure my '88 Toyota has been running just fine for a quarter century now - what could be more reliable than that? Comfortable you don't get in trucks, unless your standards of comfort are much different than mine. As for paying more just because you can afford it...
From a pure money-savings stand-point, I completely agree. That being said, I walked away from a roll-over accident just shy of 3 weeks ago because of the side-curtain airbags (my 2006 Tundra was american, so it has them, whereas the canadian ones didn't have them in until 2007). If they were available in an older model, I would consider it. Or if I was just looking for something to haul construction materials around/make dump runs.
I have taken driver's training, mentally active driving, and winter hazard driving in recent years for work; In addition, I had 4 ice tires on as well, with less than 20,000km into their 100,000km life. There wasn't much I could have done to avoid rolling, seeing as I was going less than 60km/hr, beyond not being on the road at all, which was a requirement of my job at that moment.
I found my 2006 Tundra to be quite comfortable to drive for long distances as well. I need to be able to haul 8 large rubbermaid totes of work gear, through the snow, summer mud, and down the highway, which eliminates most lower-cost SUVs as well, unfortunately.
I know this sounds like a lot of excuses/whiny-pants complaining to some, but to me, it's a perfect compromise between the new $50,000-$80,000 trucks most of my competitors drive (bought on credit), and a 1988. It is a 100% write-off for my business, for tax purposes. My Dad is also a mechanic, and will do all the maintenance for parts-cost only (and baked goods). And of course I can pay cash, without batting an eyelash. (I could pay cash for a brand new 2013 Tundra Limited if I really wanted to, but I don't).