Depends on what type of pain these boots are giving you
If you're getting pressure points on top of your feet, new insoles will likely not make a difference for you. But if you're having pain issues with the under side of your foot or maybe even your muscles, then you should maybe try insoles first.
And ya, you just gotta try on a ton of boots and let the boot pick you. I have Vans Cirro boots and they're starting to get pressure points now that they've been ridden for a season. I'm getting lace ups next time, screw boa
"When I do good, I feel good; when I do bad, I feel bad. Thatís my religion." - Abraham Lincoln
Moral of the story: If your going to rob people, wear a diaper.