There’s a fine line between frugality and being stuck in a local optima. Sometimes, expensive things are better in the long run, because they serve their purpose better and last longer.
Second order frugality: Buy it for life. Quality over quantity.
Third order frugality: This inert matter is not nearly as interesting as the people who wish to sell it to us want us to believe.
This of course after having spent too much on high quality "stuff" with little use.
It's definitely happened to me multiple times. And I don't think it's just a coincidence, with any new hobby or skill you will start out improving very quickly and then eventually hit a plateau. The first thing you think when you hit the plateau is "I would be a little bit better/have a little bit more fun with this if I had better gear", and it's usually true and you do get a slight boost. But then a little while after that you hit a sustained plateau anyway and that's the point where you'll often lose interest.