I would think if you only play Dingwalls, that going to an unlined Dingwall fretless would be to some degree easier than a parallel unlined one (the move to fretless notwithstanding). I think unlined looks cooler, is more immediately recognizable that you're playing fretless, and shows a certain level of skill (assuming you actually play it properly

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I've got a fretless 5. I'm not there yet to try to make the jump, but I think an unlined Dingwall would be awesome. I like the idea of dots on the side and on the edge of the fretboard, though I think only dots on the side would look better.