Did another boat dive with a surface interval, Valsalva just does not work. At the point I feel the pressure starting to change, it is too late.
I chewed gum on the way to the marina and I was able to perform a hands-free Toynbee around 30ft (for some reason I decided swallowing sea water was better than trying to eject it through the second stage) and freaked myself out with how loud the hiss in my ears was, so I let go of my nose and kept using the technique with no hands. Whoever said to kill an hour trying to stretch out the tubes, you are awesome (and so is gum, apparently)! Getting down to depth is a bit tricky still, but once I get down to the planned depth I can just keep doing hands-free Toynbee as I go over reefs.
Did goof up the buoyancy as well, started a semi-rapid ascent when the bladder wouldn't empty. Caught myself after ascending 15 feet and all was fine. Second dive I was able to perfectly balance my buoyancy and had to make 0 adjustments once I hit depth.
Just wanted to say thanks for the tips I've gotten from everyone here. I do see now equalizing is something that will become more natural as I use it more, and finally I'm able to get to depth with only some mild ear pressure discomfort (ascend and try again).