I'm the new guy here but what the hell, with my countless years on both 2 and 4 strokes I'll put in my $2.02 cents in.
Maintinence wise there is a quantum leap in cost. Two strokes are way cheaper to maintain than NEWER 4 strokes. Todays 4 strokes are aimed at the factory sx/mx racers who have mechanics who are paid big bucks to tear down the bike and rebuild it every race. Mr. and Mrs. "don't know squat about bike mechanics" are gonna give 3 mortgage payments to have maintanence done on all the families bikes by qualified techs. On the other hand I've owned and raced old XR600's, the old KLX650 (the one that came out in 93 and weighed 3 tons), and a DR350 for a short time that I almost never had to touch. Older 4strokes would last forever with almost no maintanence as long as there were no big engine mods made (remember the Honda XR680 they built for the 1992 baja 1000 to compete with big green? That bike ate itself from the inside out to death). But those older 4 strokes were aimed at the families out for trail riding fun. MX, SX, Desert, Enduro, GP's, etc, were dominated by 2 strokes, with the exception of Scott Summers' XR600. But there is a good example, Scotts XR motor was in virtually stock form and would last through an atom bomb explosion.
Then a few events took place. Team Green pulled out of Baja due to the death of my good friend Danny Hamel and Honda began to dominate the great race which also inspired the birth of the new and improved XR650. Yamaha built a prototype YZM400 for a young man named Doug Henry to compete with in the SX/MX series. Many factors such as our good friends the EPA forced the evolution of the 4 stroke. The factories looked to the future and dumped large amounts of cash into the development of COMPETATIVE 4 strokes leaving less money for the development of the 2 stroke. However that development like I said is aimed at the large factory racers. And for those of us who want the great handleing advanced machines that our factory hero's ride then we had better be prepared to fork out the cash to pay the "4 stroke overhead". But don't fear, if you want a good 4 stroke trail bike for the family that is very maintenance cost effective, Honda still makes their low maintenance XR50, 70, 80, 100, 250, and 650. Kawasaki makes its KLX 110, 125, 300. I'm not gonna list all the other factories that make effective family trail bikes but you get the picture. Thats why older 2 strokes are so fun. The cost of maintenance is reasonable, and if built right and maintained right (two strokes are sooooo easy to work on by the average schmuck like me), you can have a good handling bike with tons of power that will last you till Y3K. Thats my opinion which is why I have an older 97 CR250, 98 KX500, and my wifes 99 KX80. These bikes are low cost to maintain and they have plenty of grunt.