[surfgeorge]

A common theme I'm seeing from this is that it needs it's own amp/DAC to perform well. Are there any other options than the B400 within my price range that perform better than the Comet/B400 for my needs?

On that subject, IMHO the source quality is as important as the quality of the speaker/headphone/earphone.
My experience is that a good headphone will immediately sound good even with a phone as source, but a good source will make me enjoy that sound signature a lot more.
The differences are rather subtle and not always easy to detect in a short listening session, but they really make the difference between feeling annoyed after some time or just wanting to listen to music more and more, being "sucked into it", just wanting more and more.

I spent 370 Euros on a Mojo, 140 on a simple DAP, and 350 on my most expensive headphones and I would do it the same way again.
But you can get good IEMs now and add a DAC later! The journey never ends

 

[BRSxIgnition]

Hm, I drove it straight from my iPhone 6S + TIDAL in-store with no problems. They sound really great.

Check out Headphone Bar and see if you can demo it there.

Unfortunately it doesn't seem like The Headphone Bar carries those.

They do, however, carry the Campfire Audio Orion and the Shure 425 - would either of these be worth the extra cost over the Brainwave B400s for my needs? (+$170 & +$80 CDN respectively.)

But you can get good IEMs now and add a DAC later! The journey never ends

For the foreseeable future I'll be driving whatever I get straight out of my phone or portable device - not planning to carry around an extra amp or DAC, etc, for something that's meant to be fuss-free and portable. (But I do appreciate the advice and if I decide to go deeper I will definitely consider it!)

 

[Colors]

I’ve actually tested the Shure 425 and they have incredible comfort and isolation. It’s very mid-centric (nice vocals). I liked it. Try it out!

I’ve never tried the Campfire Orion but I’ve heard good things about it.

 

[BRSxIgnition]

I’ve actually tested the Shure 425 and they have incredible comfort and isolation. It’s very mid-centric (nice vocals). I liked it. Try it out!

I’ve never tried the Campfire Orion but I’ve heard good things about it.

Both of these sound promising, I'll have to try them as soon as I can - probably Saturday morning - do either have notably good bass impact at all?

I especially like that the Shure come with a Bluetooth cable included, should I ever prefer that extra portability.

I hope The Headphone Bar still has demo orions in stock to try out, since they're sold out online.