Dang, thanks for all the tips everyone!
At this point I'm gonna go get fitted for orthotics first and see how that goes. Maybe trying a NB or Adidas shoe will be the next step.
Orthotics are the best thing you can do for your feet, but they will make it a little harder to find the right shoes. If you're planning on getting them, I would get the orthotics first and then do the shoe search by going to the shop and trying on a few different models with your orthotics in them. Your shoes won't fit the same with orthotics in as they will without them.
What's worked best for me is cupsoles with good midsole cushioning and a medium thickness removable insole. I remove the stock insoles and put the orthotics in their place. Mid and high top shoes will make this easier, but you can make a low work if you find the right one.
I've had good luck with my orthotics in Nike Dunks (Mid/High only), Adidas Tyshawns, and Vans AVE's. You also may have luck trying NB Tiagos if your foot is the right shape. I can't vouch for them first hand, but the Spanky Emericas and Adidas Superstar/Pro Model and Forum would also fit the criteria here.
I'd steer clear of vulcs in general, but especially the ones that are the 'thick insole on a thin outsole' type, like the Vans Skate line. If you replace that thick insole with a hard orthotic, you have no cushioning. You can get away with those as chillers, but you probably won't enjoy skating in them.
I've tried both custom orthotics and FP Gamechangers. The Gamechangers didn't work for me, but I have some pretty bad chronic issues with my feet. If your feet are in better shape than mine, they may work for you.