I'm also working with TYPO3 over 10 years now, which until v7 and v9 was a love-hate relationship. The entry-curve to learn and deeply understand the system is just very very high (compared to other systems), but that is nothing to complain about because of its amazing stability, flexibility and quality. Now (since v9) the core and the ext-dev improved so much that I mostly love it. But still the ext-dev is sometimes very frustrating and wasting hours of life-time because of strange errors, that is my biggest thing to complain about. Even in Dev mode, its super annoying to always clean the cache if you made changes in files like ext_localconf, but not for changes in TCA overwrites. Or why changes in models are applied immediately (without clearing cache), but if you change some annotations inside the model you have to clear the cache again, otherwise very strange reflection errors are thrown which are not helpful at all (I lost hours of my life tracking this down how to deal with this and what to do, or where the issue came from). So the workflow for extension development really need to be improved, to require less learn-from-try-and-error experiences for issues like the above.
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I'm also working with TYPO3 over 10 years now, which until v7 and v9 was a love-hate relationship. The entry-curve to learn and deeply understand the system is just very very high (compared to other systems), but that is nothing to complain about because of its amazing stability, flexibility and quality. Now (since v9) the core and the ext-dev improved so much that I mostly love it. But still the ext-dev is sometimes very frustrating and wasting hours of life-time because of strange errors, that is my biggest thing to complain about. Even in Dev mode, its super annoying to always clean the cache if you made changes in files like ext_localconf, but not for changes in TCA overwrites. Or why changes in models are applied immediately (without clearing cache), but if you change some annotations inside the model you have to clear the cache again, otherwise very strange reflection errors are thrown which are not helpful at all (I lost hours of my life tracking this down how to deal with this and what to do, or where the issue came from). So the workflow for extension development really need to be improved, to require less learn-from-try-and-error experiences for issues like the above.