I have absolutely no problems with comparing drivers of the past, present, or future. The much ballyhooed "modern era" of NASCAR boils down to two things in my point of view. The schedule changed and the money grew. The cars did not undergo some miraculous overnight transformation simply because Winston lent its name and money to the series.
As for Kurt, in my mind he always reminds me more of DW, brash, outspoken, take no prisoners, ****y, catch me if you can, pass me if you dare, I don't care how long you been racing attitude. And can flat out drive a racecar.
Put him a car that handle like a dump truck, he'll drive it like it handles like a dump truck. Put Fireball or David in a sleak aero carriage and they'll drive the dem wheels off it too. Give 'em a steering wheel and a gas pedal, they will race it.