I don't think there's any Canadian maker of portable digital players. The headphone world is my main area of interest, and I daresay I'm probably the most crazed headphone user in this circle (if not all of Audiocircle based on what I've seen, though there's one guy who'd give me a run for the title).
As thrilled as I'd be to see Bryston enter the headfi game, it's a bloodthirsty market being dominated by cheap Chinese daps. I've had a couple of the more upscale ones run through my hands recently on review tours, but have been seriously underwhelmed by their quality, but hype matters more than actual quality sometimes (sadly) and there are a ton of "questionable" reviews that all sing praises for undeserving gear.
But as I was saying, as thrilled as I would be to see Bryston enter this market, I think it would be a very risky move for them. For one thing, they don't make anything that physically small. That's not to say that they wouldn't have the know-how to design something, but the infrastructure required is going to be quite different. Different casework, control systems, DACs, amplifier, etc. There's also a huge software and support side that'll be required. These all add up to big costs and high risks.
There's also the question of demographics. DAPs tend to be the playground of young urbanites who don't have the space for speaker systems. With the exception of the BHA-1, Bryston does not have much of a foothold in this realm. So now we're talking a large expansion of infrastructure, high costs to enter, and it's not even tapping strongly into their existing demographic. I'm not saying it's impossible, but from an armchair-analyst point of view that raises a ton of warning flags. That all said, if Bryston decides to dip their toe in the game, I'd be more than happy to offer my thoughts about the portables market.