I've been to a few CanJam events and have heard countless headphone amps at every price point. It is a bit subjective but a couple of headphone amps really stand out.
The Schitt Lyr 2 sounded great at only $449. It was a huge improvement over their cheaper amps and I couldn't notice any significant improvement going up the line. They are now onto the Lyr 3 for $499 which I have not heard...
If you are willing to stretch your budget a bit, the Woo Audio WA6-SE is one of my favorite amps. It is significantly better than the WA6 and is $1199. Sometimes they go on sale for 10% off retail. The stock tubes have a reputation for being disappointing so you would also have to budget for nicer tubes as well.
I haven't heard it myself but many people really love the Bryston BHA-1. The retail is $2195 but they can sometimes be found on the used market for around $1000. I think they even have a 20-year transferrable warranty!
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