The old Boeing windows (707, 727, 737) were fairly easy to open and close but if they jumped track and you didn't know how to get them back it, it could be a problem.
The windows on the 757/767 were also easy to open but after a while management at my old house said, "DON'T OPEN THEM."
The windows on the DC-9/MD-80 were also easy to open and the knob to open them was a real jewel of engineering.
Most likely few open them now because management said no reason they need to be open. Still.. on some days it was really nice to open the #2 and enjoy the breeze.
FWIW, the 707/727/737 windows could be opened and closed in flt without too much problem. No, there was no blast of air coming IN the cockpit.