Another fretless vote from me! One other thought about advantages, the Ubass is so light that I recently had to go wireless because with the Ubass the cable weight and drag on the floor became unbearably irritating and burdensome....

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Thoughts on installing a strap button vs tying around the headstock?
Now that is funny. What wireless didja go with and how much?
Dougness,
For what it seems like you are after, maybe a SUB or Cali solid body U-bass is the ticket. It has 24 frets. I also agree that a fretted one would probably be most appropriate for trying non-stock strings.
I am waiting for a flatwound nylon or metal string with a flexible core to get even closer to the upright thing ;-)
Thoughts on installing a strap button vs tying around the headstock?
Kala was great about sending me replacement D and G pahoehoe strings, but the intonation at the 12th fret was still off. The thunderguts were nearly perfect, and the pyramids I'm still waiting for should hopefully be even better.