...coming in late to this one...
I've got club feet (Tallipes deformity), extra super tiny feet AND the long second toe (foot size is a 35-37 metric, toe size can make me go up to a 38).
My feet hurt a lot and have for years, and I live for shoes that are comfortable all day.
My best recommendation is to find a BRAND that works for you. For me, Eccos are the best. No, they are not cheap, but my first pair lasted *3 full years* of living and walking in New York City, and 7 years later are old and battered but still wearable. Merrells can be OK, and some Skechers, but Eccos are far and wide the best shoes for my feet. The best Eccos are the 'receptor' line with heel stabilizer and metal lasts.
Other people I know with foot problems like Danskos, New Balance, Birkenstocks, Avia, and other 'health' shoes. Again, you should expect to pay around 100 $ for them, but most of these brands are built to last.