In my experience, it's been more of a matter of a language being obtuse, poorly designed (aka lack of basic computer language structures and syntax) or having bad/annoying development environment design.
The most annoying I've worked with was Gupta SQL Windows. I had to learn an old version of it to support an important legacy application where I worked at the time. The files were all binary, which made compares and searches difficult to impossible. The IDE, which you had to use to do any development, was outdated and clunky. It was inadequate for the 90's much less today. Even entering a line of code required a complex set of keystrokes and it was easy to make typos and it was difficult to undo them. On top of that, the code was poorly designed since it was originally written by a mechanical engineer with no experience in software development.
So far as learning curve, I'd say it was when I was learning C++ and gaining an understanding of OOP during the mid-1990's. This was a big jump from the earlier procedural programming I had done in MASM, C and QuickBasic.
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