My approach is to always buy the first "stuff" cheap and then try to use it the best possible way. If it breaks or I see the limits with the "stuff", then I go for the good and expensive one. This way I know I need it but I can also better assess the quality.
This of course after having spent too much on high quality "stuff" with little use.
The only problem with this approach is the amount of time before your interest in a new thing starts to fade is often just about the same amount of time it takes to recognize the limits of the cheap stuff and decide to upgrade.
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.
This is what I do with tools. If it's obviously something I will use again and again, I'll pay for quality. If it's something I might need just once, but not certain, I'll buy a cheap one to get the immediate job done. If I need it again and it breaks, I've now needed it twice so I'll replace it with a good one. (If it doesn't break, it's a better value than I thought).
This of course after having spent too much on high quality "stuff" with little use.