I am also a one set up one pair of shoes guy and always dread to change well worn in items out of fear I will not be able to skate as well with the new ones as with the previous ones or it will take a long time to adapt. The nightmare scenario is to change deck and shoes simultaneously.
Same.
I keep one main setup going. I do get bouts of madness and swap stuff out just to try it, but I always come back to:
F4 99s. Prefer a square profile (tablets/conical/etc), but will skate classics. I used to like small wheels but over the past year I moved up to like 54-56mm so they'll last longer. I started running a 1/8" riser too.
Ace trucks. Tired to go back to Venture a few times out of nostalgia but I always end up with Aces.
Boards are a little more varied, 8.5"+ pop or 9"+ shaped. I'm not good enough for WB to matter that much but if push comes to shove I like 14.5"+. Overall length is more important, I like 32"+. Right now I only have shaped boards on deck, but I'd be open to a bigger pop down the line.
Currently running an Antihero Cardiel 9.18 football with Ace AF1 77s, 1/8 risers, and 54mm 99 F4 tablets.
I skate mostly curbs, with some flatground thrown in the mix. I need a setup that is good for slappies, power slides, and all the other non-tricks that I like to do. I think any time I've varied from the stuff above, it has been because I was trying to skate a way that isn't really me.
I have a cruiser, but it is basically the same shit but with keyframes instead of spits.