44 years on bass, nearly 2/3rds of those on 5-string. I started playing bass in 1967, and started gigging out in 1972. I eventually reacted to the growing prominence of synth bass by putting a Hipshot detuner on my '64 P-bass (IIRC, it was some time in the late '70's), but I wasn't satisfied. I finally saw my first 5-string around '82-'83, and sold my P-bass shortly afterward.
I've had a few 4-string project basses since then (just got a Squire VM fretless Jazz), but I always get frustrated and flip 'em after a few months. Ditto for the one 6-string I bought.
I know a lot of guys struggle with the transition from a 4-banger, but to me, it felt right from the first time I picked a 5-string up. The wider fingerboard didn't bother me, and I found a bunch of unexpected benefits. I find transposing easier on a fiver (I always hated having to spoil the shape of a riff by popping low notes up the octave). I also liked the freedom to cover a wider range of notes without shifting position, and once I got my amplification sorted out, those low C's and D's were pretty satisfying on some material.