I had the same thought when I turned 40, except I was neither a pro nor likely to be mistaken for one. I had been through several J basses and ended up selling them all, so I decided to order a Sadowsky NYC Ultra Vintage Jazz to end the search. It was a beautiful bass, but I never really bonded with it and ended up realizing I just prefer P basses. So I traded it for cash and a Lakland P/J that I love and still have.
I recognize that none of this answers your question. You already have a Pino so you know how good the Custom Shop instruments can be. But you also have a Will Lee so you've got the Jazz thing covered. I'd go for a custom shop P bass with rounds, myself. I recently acquired a Sean Hurley signature P and it's amazing. Same quality as the Pino plus it has the foam mute you can flip on or off. Vintage is great but hit or miss, and at some point I'd be worried about gigging with a vintage bass you couldn't replace.