I’ve spent thousands upon thousands of dollars on headphones and DAC/amps throughout the years. If I could go back in time and just get my forever setup and not wasted all the money, I’d have gotten me a nice pair of IEMs for ease of use, and spent rest on a banging stereo setup. Even modest speakers are more enjoyable to me than the best headphones I’ve tried.

But to answer your question, no, you will never be satisfied even if you start at the top. There will always be someone else’s glowing review that piques your curiosity, some new headphone with new tech that manufacturers claim revolutionize the industry. Even if you hold off at first, see enough ads and read enough impressions and your curiosity may get the best of you. And that’s ok, because the hobby is fun.

If you have to start at the top (or near it), I’d buy something that’s EQ’able like a nice planar from Audeze or HifiMan, even the HD800s. Then spend your money on a decent DAC/amp combo that allows EQ profiles like the RME-ADI. You can even go cheap and get a cheap DAC and connect a Minidsp in between it and the amp to use EQ profiles.

I have:

Arya Stealth v3: desk eye candy. Will probably keep for PC gaming as needed

64 Audio A12ts: barely used last few years, may buy some Bluetooth wireless modules to increase usability in the future

LCD-X (2021): probably selling soon

Shokz Openfit: use at work or out and about

Apple AirPod Pros: use at home in bed or around house

Sony WH-1000XM4: barely used anymore, too big

Ananda: bought for my wife’s gaming PC, which she barely uses. Probably sell soon

HD650: OG love, modded. Probably keep since can’t sell but barely used anymore as well

I used to use headphones exclusively. Note that I have a home theater/stereo listening station, don’t really have use for headphones anymore.