I'll vote for the ease of playing with an amplifier.
I'm with you Ric. But, here's a story. I played with the Chicago Jazz Ensemble, a full big band, off and on over the years. It was directed by Bill Russo of Kenton arranging fame. We had a concert at a large club and I brought my little Bloc 50 amp with 10" speaker, while using a single element Underwood pickup. The whole band including drums was mic'ed.
At rehearsal, Bill kept asking me to turn down until finally, my amp was off. I had to play the gig unamplified. Of course, the most frustrating thing was that I couldn't hear myself, and my bass isn't particularly loud acoustically, but we all know that the sound of a double bass carries into the audience, so... An older school guy like Bill Russo is going to have a different bass sound/mix in his head than younger musicians, I concluded.
To the OP, yes get a pickup. It's today's standard. There are countless threads in the forum regarding most of the available pickups and amplification choices on the market.
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