So, of all the replies in this thread, this one spoke to me the most. I think you're right. Thank you for describing it so well.
I started out a little after you did, with BASIC on a Commodore Vic-20 and Commodore 64, then Logo, then HyperTalk, and so on. I used to have fun decompiling programs and poking them with MacsBug to make them dance for me, and I used to have fun writing my own toy operating system and generally just screwing around. And, for the most part, my tools were simple and reliable.
So that's what I compare everything now against, and it all seems less reliable and more complicated. MacsBug was a thing of wonder and beauty compared to the "debuggers" I have to deal with most often now -- Firebug and GDBp. And I've started working recently on building my own tools, which is sort of fun again, so maybe I'm sort of headed on the right track.
But anyway, thanks for describing it like you did.