I started programming with basic and then DOS and assembly. I have very fond feelings and deep knowledge from both of them, but the UNIX generation rightly looked down on them as 2 turing tarpit hellholes.
Onward to C, with Mix, Watcom and DJGPP. Better programs, but you live with some stupid inefficiencies that wouldn't fly in x86 asm.
Onward to Win3.1 and Win32. The end user experience is much better, but as a programmer you now have to accept control by the OS over your work. You can't just e.g. write to VRAM anymore. First serious dark clouds appeared for me when I realized Microsoft cynically used us all to extinguish all competition. Politics had entered my IT life.
Then came the web. In one way, it was glorious, but programming it in javascript was a serious hellhole. jQuery brought some sanity, but the user friendlyness from windows was almost impossible to reach.
Serverside was java, which was dog slow until hotspot appeared. It eats memory like there is no tomorrow. Sun dictated the very shape of your program. There was some war going on between EE which was horribly verbose, and Spring which was geassroots and looked down upon by the architects, as if it smoked weed or something. Whatever camp you chose, pain would follow. Ir you could go to the PHP camp and spend more time debugging than programming .
There was some python here in my life, good but dog slower than even Java.
Then nodejs. If you thought Java gobbled up memory, you'd just die working with that abomination. End user usability had still not recovered from the win95 days (it never did). You had no type safety with javascript. In fact, every decent tool and technique was sacrificed on the altar of equal back and front end language. Then came frameworks like angular where v2 managed to commut ecosystem suicide, and react. Meanwhile transpulers packers etc managed to undo much of the noneedtocompile of javascript.
In the mobile world, 2 massive companies appeared, and their app stores killed any liberty of publication.
There us more, but I ran out of time ;-)
All of this is quite ranty, partially deserved but there is also quite a lot of good in here. Even so, programming for me was most fun on DOS, and user experience on win95 to xp.