I am not a flight instructor but I have flown airplanes as old as a 1942 model and as new as a 2005 model so perhaps I can contribute in a meaningful manner. If a flight instructor or older aviator of extensive experience knows better I’m sure they’ll say something.
To an extent, all airplanes across that time span fly the same. There are some minor differences - joysticks vs. yokes, for example - but that’s about the same difference between a gearshift on the floor and a gearshift on the steering column. But, for the most part, the same motions are going to get you the same results. For the most part.
My impression - based solely on my limited but varied flight experience - is that the newer airplanes are more forgiving. By which I mean mistakes on the part of pilot, or deliberate excursions to the edges of the flight envelope, are less likely to be alarming than in older airplanes. For example, although I did not stall the 1942 vintage airplane I am told that it tends to stall all at once and rather abruptly. The 1960-70 era of airplanes do noticeably drop during such a maneuver, but are easily managed/controlled. The 1970-80 models were even more docile. The 2000-2005 airplanes’ “stall” were more of a gentle settling. It also became progressively harder to stall the airplanes as you marched through the years, making an accidental stall much less likely. For routine flying - normal take-off, landing, and en route flying - the handling is pretty darn similar. It’s the flying outside of normal straight and level where the differences seem to show up.
Likewise, it was my impression that as the years marched by there were continual, small improvements that make piloting an airplane easier. By the 1950’s the layout of certain particularly useful instruments on the panel were standardized. By the 1960’s tricycle gear became much more common, reducing the incidence of ground loops, taxi accidents, and made take-offs and landings in crosswinds less of a chore or risk. I did notice an unfortunate trend between 1970-80 to less and less window, but that seems to have reversed, to the point that the airplanes I flew that were designed past 1990 have more and more window allowing for better visibility during flight.
Airplanes have become lighter and more fuel efficient, which reduces hourly operating costs. It’s almost unheard to have to handprop anymore, aside from experimental and/or vintage aircraft - given that a prop is typically 50-70 pounds of stuff shaped into something like a blade that swings around 1200 or more time a minute, I’m sure you can see the hazard in standing close to one while starting it. Electric starts are safer. We now have on-board parachutes available in some new airplanes for catastrophic accidents (which can even be retrofitted to some older models) and even airbags (on an airplane, the airbag is in the seatbelts, not on the “steering column” thingy). Seats also seem to have gotten better over time, at least from the standpoint of comfort, particularly past 1990.