Well, the pickup height adjustment is a good tip. I pulled the '59 away from the strings a bit and I can definitely hear both pickups in parallel now. I'm going to play around with what spacing gets me the tone I'm happiest with in that position and debate going back to a 3-way instead of a 4-way switch.
Thanks for all the tips!
I am happy that worked well. Sometimes you don't have to buy anything new at all.