Rockbox Ports are now being developed for various digital audio players!
In regard to the second question "How would I trivially weight random playback of all tracks?", you've got it exactly. Insert the most desirable directories/albums/tracks/artists into the playlist as many times as you would like to to increase the odds of playback to your liking. You wouldn't need to insert shuffled, as you can shuffle/de-shuffle/re-shuffle during playback.
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