I voted "yes". I have played PB several times over the years. It's more than just an 18 hole round of golf. Especially if you get one of their better caddies.  When you get done with PB, go play Spyglass Hill. This is the tougher of the two courses imo.  That whole area is a golfer's dream "golf destination". You don't worry about the costs. 

Putting is all about hand to eye coordination. How do you know how to throw a ball to someone 60 feet away? Expensive putters are the biggest joke in golf. It’s an almost flat piece of metal on a stick. I have a lot of gear and I might use a Betinardi one day and a Dynacraft the  next. I don’t think I have a putter I paid over 40 dollars for. It’s personal skill. Some of the big mallet heavy stuff just complicate things. 

When in doubt, just ask the counter guy, and/or the starter. Example would be "I'm a 10 hdcp. Which set of tees do you recommend for this course?" On more than a few courses, the color of tee boxes won't matter very much. These would be courses where the different tee boxes are really close together.   

Hmmm...  

I'd pay it to play Pebble. But if I were doing that, I'd set aside like $3k-$4k so I could fly out and play a bunch of northern/middle California courses at once. Pebble, Spyglass, Poppy, Spanish Bay, Pacific Grove, Pasatiempo, TPC Harding Park ... definitely missing some. I wouldn't just fly in, play Pebble, and go home.