Here’s my take on it:
This hobby is in my opinion all about how insane are you. How enthusiastic? How far are you willing to take it?
If you are just a consumer, you will be happy with something that doesn’t hurt your wallet. “Doesn’t hurt your wallet” is subjective. If your salary is 1000 bucks, a 200-500 bucks is not a small sum of money (depending on how much it matters to you). If your salary is 10000 bucks, you are probably comfortable to spend 1000-3000 bucks on your setup.
The other aspect is how crazy are you about the hobby. How much does music matter to you? How much does gear matter to you? It could be either of those two, or it could be both. There are gear enthusiasts, there are music enthusiasts (listeners), and then there are both of those combined. If listening to music, or the gear itself, is very important to your life, you are probably ready to save up and spend more than an average person. This means that if your salary is 1000 bucks, you might save up some money and buy a 3000 bucks setup.
How much are you willing to spend to pleasure yourself? How much does it take to please yourself? You see, a lot of people here can be happy with a Sennheiser HD598 or a HD650/HD6XX, but there are people who like the luxury of high-end. Think of it as an addiction.
Speaking of luxury, it comes with an invisible tax. When something is exquisite and abstract, luxurious, it costs more. Not because of the performance, not because of the materials, but simply just due to the exotic nature of luxury. Exclusivity costs.
Whether or not you need this luxury is entirely up to you. I strongly think this hobby is individual. People spend their money on fine clothing, fine food, drugs, women, gambling, computers, cameras, cars, vintage things, there are a lot of things that people spend their money on, a lot of things that evoke pleasure, in our case it is things that produce sound.
At the end of the day, I think the #1 most important thing is that you are happy and can sleep well at night. If you spent a lot of money on something and it is not making you happy or it makes you feel guilty, it simply wasn’t worth it.
Stay happy, and enjoy yourselves!