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What complications did you not expect when going fretless?

Sorry mate, I could have been more clear. My rounds were chewing threw my fingerboard so it was an easier option to switch to flats.
With good fretless technique that is rarely an issue. (How do you do your vibrato?) Yes, eventually there will be some wear marks, but in the 40 some years I've been playing fretless bass it never got to the point of needing to dress the board. Of course, avoiding rough feeling strings (for example, Rotosounds) make a big difference; D'Addario Xls work well (I have not tried many other brands on fretless basses, other than TI Jazz Rounds). As to the TIS, if you can get along with the very supple feel of them, I highly recommend those strings. Great tone and feel (to me) and they are very gentle on fretless fingerboards.
 
With good fretless technique that is rarely an issue. (How do you do your vibrato?) Yes, eventually there will be some wear marks, but in the 40 some years I've been playing fretless bass it never got to the point of needing to dress the board. Of course, avoiding rough feeling strings (for example, Rotosounds) make a big difference; D'Addario Xls work well (I have not tried many other brands on fretless basses, other than TI Jazz Rounds). As to the TIS, if you can get along with the very supple feel of them, I highly recommend those strings. Great tone and feel (to me) and they are very gentle on fretless fingerboards.

You called it; I used Rotos then. It was also a fretted conversion with a cheap board wood. I used vibrato the same way I would on a cello or double bass. It wasn't the best specimen of a fretless, but I enjoyed it for a couple of years. Ended up getting rid of it. Can't remember what the board was made of though.
 
I'm really curious into diving into that realm even though I'm just a novice and wanted some advice from those who play fretless?
I defretted my '59 Jazz (yes they were released in1960 but mine is dated 1959 on the neck so....) in the 70s during the Jaco craze. Now the issue is the old epoxy drying out, and rising up from the fret slot, resulting in an annoying little buzz.....easily remedied by filing with steel wool. Very tiny and intonation challenging on a Jazz neck up top. The hardest thing about playing my bass is NOT sounding like Jaco!
Front Fenfer.jpg
 
I defretted my '59 Jazz (yes they were released in1960 but mine is dated 1959 on the neck so....) in the 70s during the Jaco craze. Now the issue is the old epoxy drying out, and rising up from the fret slot, resulting in an annoying little buzz.....easily remedied by filing with steel wool. Very tiny and intonation challenging on a Jazz neck up top. The hardest thing about playing my bass is NOT sounding like Jaco!
View attachment 3530370

Is this an original fingerboard? Why are there no dot markers on it?
 
Regarding sliding, imo it shouldn't be the default way of playing a note on fretless. It should be chosen for expressive purposes where it fits and doesn't interfere with the music. A good fretless player should be able to make the bass sing like we all love with fretless, but should also be able to play such that no one knows they're playing a fretless.
Yep. Best way to fix sloppy/lazy Fretless technique is to practice playing scales while using a tuner. Develop some muscle memory of knowing where to put your fingers - it makes Fretless sooooo much easier & heaps more fun to play.
 
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I briefly owned a Rob Allen MB2 4 string. Lovely sound and easy to play, a wonderful piece of kit, but sadly I was straying too far out of my comfort zone. No frets, no low B and, sadly, a lot less muscle memory than I expected!! I made a reluctant executive decision and went back to fretted 5 string.