hm
Just about to turn 23 and I have a terrible knee problem from a fall at work, so My knees and feet tend to bother me. Personally I love wearing Etnies, DC shoes, or just about any other GOOD brand of Skating shoes. They have thick insoles made to absorb impact from skating, good quality [ the pair i'm wearing now are 3+ year's old and look brand new] and they aren't terribly expensive. Custom insoles would help a bit more, but i have to say its gonna be about what you find comfortable.
Most people find skating shoes to be too wide, and they are for a majority of people, but I'm size 12W in the feet and these are perfect. Otherwise I say a pair of Krocks or cheap knockoffs are also comfortable as they eventually mold to your feet. /shrug. Good luck on your search for perfection sir. /bow