Heya,
If you're interested in getting high end sound on a dime, I would explore the Hifiman HE-500 and the NFB-12.1, that's $900 new with some shipping added in. The HE-500 is not overly bright, it's very natural sounding, with superb mids, and warm deep bass, holds flat and strong all the way to 30hz before it starts to roll off, still does 25hz even, but it starts to fall there. It's very clear, crisp, again, the most natural sound I've heard out of a lot of headphones. Comfort is subjective, I find it comfortable enough to wear even for a heavy headphone, and I have both velour & leather pads for mine, I'm using the leather pads a little more lately just to see how I like it compared to velour. I like both so far, not much difference other than how it feels. The ortho isn't going to have quite the "3d-esque" sound stage of the T1, but the T1 is also brighter. So it's a little trade either way. I really recommend the Hifiman HE-500 with the NFB-12.1 though if you want to save a little money. When you compare $1k to $2k you expect a massive difference, but really, it's a tiny, tiny difference. And frankly the T1 is not better, it's just different. So unless you want to drop the money on the T1, I would definitely go Hifiman.
And if you really want to experience a similar ortho sound on a dime, the Hifiman HE-400 with a simple Fiio E10 will make you wonder why people spend more. It's that good.
But if entering high end, I definitely suggest Hifiman HE-500 and an appropriate dac/amp (NFB-12.1 is my suggestion simply because it has more than enough power and is not expensive yet is good quality). I personally run my Hifiman HE-500's on my Bifrost+Lyr and I like it, but it's significantly more, and frankly, not that much better when you look at cost for performance. For $900 new, the HE-500 and NFB-12.1 is very difficult to beat for a high-end setup on a dime.
Very best,