Shorts have to work. For you, the rider. The dollars spent doesn't matter (unless you are spending so much you cannot have enough pairs to always have a clean pair to ride - an issue back in the day when the good shorts were wool and very slow drying).

I've struggled with shorts for years. Most of my issues have been about finding shorts that keep things where they belong, probably mostly a result of me being issued a less than standard body type. About a dozen years ago I discovered the Segoi shorts. Hurray! Comfort like I have never known before. Many rides I never have to "adjust" things. Even with many stands for hills and sit downs after. When I was young many years ago, that wasn't a huge issue except on very warm days but as I got older the shorts had to get progressively better. Didn't happen until I bought those Segois.

Maybe, just maybe, I could spend twice what I spend on the Segois and get a rideable short. But more likely they'll be just another cold weather pair where I am so shrunk up that anything works.