Ugh. foot pain sucks. I'm dealing with this myself. I have psoriatic arthritis with a good portion of my damage in the feet.

Here's my advice: Don't waste the money on custom orthotics unless you know the pedorthist can make them work for cycling shoes. I have custom orthotics, but they won't fit into any cycling shoes I've tried. They're just too thick. I got them before I started cycling though... I don't want to fork out the $$ for a new pair out of pocket.

I've tried the Specialized OTC orthotics, but I didn't care for them with my ridiculously high arches. They also didn't have a lot of metatarsal support, which I really need due to where my joint damage is. You might have better luck though. Other brands might be better as well.

I've heard good things about Nothwave shoes for folks with wide feet and foot problems. A lady I ride with has RA and has had them recommended by several people. Right now she wears Keen sandals to accommodate her foot problems. So, that might be another option, for summer, at least.