I fully agree. Personally, I judge differently what's clickbait and what's not (as you said, it's subjective).
If for example a title says "You can simply change your life by doing one little thing"
Then I wouldn't necessarily say it's clickbaity per se.
Next comes the subtitle, which should give you a bite of what's to come. If the subtitle only states "By using this simple trick", then I learned nothing new and have no expectations. That's when I consider it too baity. Instead of using the subtitle as a summary of sorts, the author decided to put in redundant bait. That's when I skip.
If they were a little more specific by mentioning a characteristic or approach of some sorts to underline their technique, I'd be interested in learning more about it.
As for "How to..." articles, they are a proven format that attracts readers. Same with numbers (Top 5 ... , 7 simple ... , etc.)
Those aren't inherently bad. If they deliver the content they promise, they are great (and easy to digest, too!) But those that promise you the same stuff again and again, especially in regards to how to do stuff on Medium, then I'm out.
Those articles are like sneaky politicians. They can talk for hours without saying anything at all.
I only use "How..." or numbered list articles occasionally. Most of the time, I pick a title that I personally like, even if it goes against all marketing advice.
I'm not a marketer after all. If you don't like my headlines, then chances are you have different interests, opinions and expectations than I do. I would probably only waste your time.
But I really dislike the ever same articles stating "how to make $XXXX on Medium", they all give you the same trivial advice, just in different words, often without any real proof of concept to back it up. And it honestly pisses me off that those articles get read enough to give the author $XXXX from writing on Medium. That's the real clickbait.
I'd prefer if the articles who actually provide you real advice get the reads instead of those. And I'm not talking about my own. There are plenty of authors (you included) who put out actual quality content.