I've long given up on stomp boxes for a while. I think if i see enough pictures of GAS-worthy pedals i might just go back to my pedal GAS-ing ... hahahah ...
anyway, from my previous experiences playing around with pedals, here are some pointers you could take note of in arranging your pedals.
Each individual pedal have their own purpose in shaping your tone, the basic breakdown of signal processors would be modulation (chorus, flanger, phaser, etc), distortion (fuzz, overdrive etc) and signal processors itself (compressor, limiter, expander) ... i can't remember which category synthesizers fall under, most prolly modulation but i might be wrong.
anyway, understanding at the roots what each category does to your sound will greatly help you in arranging your pedals.
when i was arranging my pedals i was asking myself whether i should "distort the chorus or chorus the distort" ... if you know what i'm talking about.
So at the end of the day it helps to know what that particular category of sound shaping it does to your tone. e.g. modulation affects the waveform by either duplicating/delaying the waveform to give you a phaser, chorus effect etc. ..
i'm not gonna give you a quick fix here because in the end you'll be just arranging your pedals to what people prefer and not know what you are doing so to your pedals. it's a bit of work but in the long run when your pedalboard starts to expand you'll find that the knowledge you have over different categories of signal processors will help you determine what arrangement will work best for you.