>>206663 yfw a 99 cent plastic poncho would've kept you dryer than a $300 Columbia "waterproof" shell.
It all comes down to trial and error for me.
Transitioned from high tops to sneakers pretty quickly. Ditched the parka for a windbreaker and layers. Opted for water bottles on the waste instead of a bladder in a backpack.
You're not going to pick the perfect equipment your first try. Just remember what works and what doesn't.