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Steve Bailey on flats vs rounds on a Fretless

I think it boils down to whichever type of string works for a particular bass. After trials with both... my passive Sire V5 jazz bass fretless sounds better with flats. My active ESP LTD 5-string fretless sounds better with rounds. Go with what works and sounds best through experimentation.
 
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Currently I use Gold White Tapes, gives me some mwah if I want it and upright-esque sound if I want. Even has a bit of black with how low I have the action.

Not sure if it's the optimal string, but the fact that it is gentle on the board (I slap in it sometimes) and matches the gold hardware is nice.

I should probably try some rounds, flats, Pressurewound, whatever else on it at some point, to see if I like those better, but I am a little hesitant to experiment when the white gold tapes are pricey and last an extremely long time. (Though I am sure I can take them off and put them on again later)
 
Steve is right- that classic Jaco/Pino tone is roundwounds. Its crunchy and authoritative and singing.

I have White Gold Tapes on my MM. They get more mwah than rounds, because they are thicker and floppier, which sounds excellent. They have enough treble on tap, although not that ringing Jaco treble. The biggest problem is they have much lower output than roundwounds, which i believe has been discussed before.