I share your view and had a similar experience with a pair of Barker shoes a few years ago. If you're looking for a nice longwing I can recommend the Herring Canning. Made by Cheaney with or without dainite soles. They are a joy to wear and the burnishing gives it a great look.
If you have room to spare in your Timberlands you should go for the 10F, but if they are snug you should go for the 10,5F. This is a very rough advice but I hope it helps a little. I don't have any other american made shoes to compare with so it's the best I can do.But I can really recommend the Kempton, a great shoe. I have it in brown suede with dainites and I just love them