That is pretty impressive. I know a few of the guys on Alden that can do that. I can name probably more for EG since they're just names though... Hell, I can easily name 12: Shannon I, II, III, IV...XII!
Chelsea boots should be snug by the instep but they're not going to feel like lace-ups due to the constructions. Comfortable should be good. If you want to fill in the gaps an insole should be fine. Nick V has a variety at his shop (VIP Shoes) and you can walk there to break in your new shoes!