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What complications did you not expect when going fretless?

One can try to rely on lines, dots, and/or "muscle memory." However, these are no guarantee when you cannot see visual cues (lights too dim or bright)...
Whenever I gig with a fretless I bring one of these and someone who knows how to use it. I never have a problem not seeing! :woot:

Super Trouper 01.jpg
 
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It's been awhile since I dug it out, and I miss it, but it can be impractical and yet I would never sell it. For me it was best in small group situations where I can hear everything clearly. And as a singer I prefer not to have sing too much and just play fretless. Fret markings were totally useless to me, as you had to adjust for each note most times anyway (subtle adjustments). Though I have used it for some blues and reggae gigs, the fretted attack is very different and necessary for most work. The standalone expression on fretless is unbeatable. Special thank you to Jaco, if not for him we wouldn't be even talking about this...
 
At first, you may be tempted to learn fretless watching the fingerboard and relying on finger positions. You must eventually begin using your ears to make sure your notes are properly intonated. Audience doesn't want to see a bassist staring at their fingerboard during a show. You really have no choice as the lighting of venues are usually low.
Jaco looked the fingerboard all the time ,result: perfec tuning and I recommend to use a lined fingerboard
Finally you only have to be careful with two things: tuning and tuning
Good luck