Just like a kid ignoring his mother's 100th warning and burning his hand on the stove anyway, your wisdom will only be had by your own trial and error. Often young riders spend all their money on the bike and then wear hand-me-downs or On Sale cheap stuff. Not saying you did per se, but I know I'm guilty of it. I haven't found any "Rain Proof" gear yet without having to make 60 payments.
I'm twice your age and I'll tell ya, going coast to coast on a bike that doesn't break down, suits all your needs, with gear that works and having everything stay in its place going reasonably well makes for a real sad, pathetic, boring Ride Report. Then you have to rely on pics and humour to keep people interested. You got that nailed so embrace the adversity!
Enjoy your quarter life crisis and make sure you out do it when your Mid life hits.