Wow! What an adventure for you and William!

I don't know anything about touring but I have a suggestion for your new shoes. I've found that it's virtually impossible to find shoes with great arch support right out of the box. Replacing the stock insoles with Super Feet can turn virtually any, high quality, athletic shoe into supportive shoe also. I usually have to buy 1/2 - 1 size larger than my casual shoe size to accommodate the extra thickness of the Super Feet insoles and to allow for foot swelling in hot weather.

Specialized also makes cycling specific insoles with extra arch support but they're more expensive than Super Feet and harder to find.