I have two fretless instruments, my 5 string MTD and a Steinberger NXT 5 string upright electric. The transition from fretted to fretless was not terribly difficult to do when you know where you are going on the fingerboard. You do have to be much more precise with your finger positioning and that does help with fretted basses.
The biggest issue for me was the finger position differences between the MTD (35" scale) and the NXT (43" scale). Suddenly the reach between the first and second position on the upright bass neck is about double that of a standard 34" bass. That took some getting used to.
Lots more subtleties that you can play on a fretless, much more like a voice than and instrument.
I play my fretless most of the time now, just bringing out a fretted bass when the music requires that crisper tone.
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Steinberger NXT5 EUB, MTD 535 Fretless, Tobias Killer B6, 72 Fender Precision
Eden WT500, WTX1000N & WP100, QSC PL230
Eden D410XLT, D410XST, 215, Fender Bassman 10
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