The ananda’s are really easy to drive. I would say the edition XS are also worth the money at $500, but they’re already so close to ananda territory and the latter is obviously better. There are definitely headphones over $300 that are worth it, it just depends on what you get. Most of them are not really worth the hassle.

Endgame for me is definitely the hd800s. It’s got all the soundstage I’ll ever crave, after eq it’s one of the best sounding setups I’ve ever had besides my higher end speaker setup, and they have resolution that gets close to TOTL stuff. It doesn’t have much bass at all though, but it’s still plenty wooly for everything out there.

What I would recommend is either an open boxed ananda at $600, or try and find a used hd800 for $700-$900. There is no harm in getting the original hd800. It’s brighter sounding, but you can take the same approach as the S version and just eq it and get the same result. Bass is cleaner sounding on those if you want a nice bass shelf. You would hardly take a loss on them, if you end up not liking them. Just because you could sell them for what you paid for them really. But it’s worth investigating. They’re a sandbox for eq because of how massive they sound on a lot of music. There’s plenty of tweaking to be had that suits your ears.

Their literal only weakness is lack of bass and dynamics, which the sundara isn’t exactly known for anyway. But if you want all the soundstage a headphone can offer, those are it. Ananda or OG hd800 would be the best bang for your buck, those are my recommendations.

You don’t need an amp for the ananda, they’re pretty portable. However, you would need a decent dac or amp for the hd800. Nothing crazy. Don’t let anybody tell you that you need a $1000 amp and dac, so long as you have a decently spec’d dac and amp to use, you’re fine