Odds are the shotgun is a Parker or an L.C. Smith, both of which could be worth the big bucks. If it's a Winchester 21, you might be able to retire. If it came with a Henry, it's likely he stayed "American" when he bought his guns.
My grandfather had one of those old Parkers, which disappeared when he died... [sigh]
About the Henry .44/40 and my dad's mulie. When he tells the story he likes to say, "That buck was about 100 yards away. I pulled the trigger and had enough time to put down the rifle and finish a cup of coffee before the bullet hit the deer."
I guess velocity was not the .44/40's strong suit.