of course. how wide are your feet at the widest?
there's no dedicated red wing shop, but a local store has a lot of models. I'll see if they have the ones you need.
Depends on the kind of boot you want. If you're looking for something sleek then I can't help you. If you want a pair of real boots that you can knock around and will last a long time, look into Russell Moccasins. You send them a tracing of your foot and they make them to order. They can even use the Munson army last, which I understand is cut wider in the toes to allow complete movement of toes and foot bones. They make primarily hunting boots but also some chukka and shoe styles as well. You can customize however you want, pick the type of leather and sole etc. Takes 4-5 months for delivery but if you're looking for something to last a long time it's worth it.
I think Chippewa makes some stuff that look like classic timberlands. Lot of it is still made in the USA. http://www.chippewaboots.com/