A couple things. If you're willing to go USB, I believe it would be fairly easy to disable the driver from loading in Linux and VMware I believe has USB support provided the host OS doesn't grab the device, so you'd be able to access the sound device directly from the guest. I don't know how well this would work, but it may be possible - then no issue, provided you don't care about the host os's sound output.
A DAC is basically just a fancy name for a soundcard that does output only. Soundcards usually have inputs, mic ports, 3d processing etc. A DAC basically just converts the digital audio signal into an analog one, without doing anything else, so no extra processing steps or inputs or anything like that. Traditionally they take an SPDIF input and give a line output, but USB variants are becoming very common.
A problem you (may) have is that they don't generally contain an amplification stage, so they can't drive headphones directly. You'd need an amplifier as well.
An AlienDAC might be a good option for you, it's a DIY project but they're very cheap parts wise, so you should be able to find a used (or even custom built) one for a reasonable price.
Regarding USB bus contention - bulk transfers that hard disks use are the lowest priority on the USB bus, so sound devices will usually fare fairly well alongside them. It's not a guarantee though, and heavy traffic might cause some problems. Most modern computers have a separate USB controller either for every port or for every set of two ports, so that helps a lot, I doubt it would be a major issue. I use an AlienDAC regularly with the portable USB2 drive I use in my car audio system copying large amounts of data with not a hiccup.