"Anyway, the old guy continually stressed the fact that 'it is a Winchester...and not an inexpensive piece of junk....." Right."
The only research he ever did was to look at the name. Later after he bought it he maybe did a web search for ammo not made since before WWII or maybe WWI. He bought it without finding out if ammo was available which is silly. He never figured out how to reload it. Perhaps he does not reload at all. He bought it as an investment or a tomato stake but not to shoot.
Ever deal with a seller who thinks what he has is worth more than you do? Or can not understand why others are not as amazed with it as he seems? Why of course you have, we all have. I find a lot of sellers just look at the name on the gun, or the fact it is old, or the fact it is odd that it has to be rare. Winchester made millions guns, sometimes a million plus in a single model. Odd is not rare most of the times, it is just a pain in the ass to feed. And condition is king to a collector with everything else being equal. But sellers often think what they think is it and the rest of the world is missing something.
I was dealing with a seller a few weeks ago who was trying to sell a Sterlingworth 12 ga. with 30" barrels. They made ten of thousands of them. And his had been dragged home, behind a pickup truck, judging from the looks of it. To me it was a rainy day shooter at best or maybe a parts gun. Worth $400-500. It was a 10% gun at best. You see them sell for that on GunBroker fairly often. When he said he would let me have it for $2,100.00 I almost choked. Just told him that was too rich for my blood. He did nothing to figure out what he had, what it was worth or even what condition it was. He kept pointing to the early patent date like they all don't have it on them. Like it was made in the same year.
I don't know what this seller was asking for his gun. It does not matter. If you don't know what you have find out about it before you buy it, or sell it, if you inherit it. Don't just set a price based on pie in the sky numbers. If you wont do that then don't get pissy when nobody is hot to buy it. Right now is a buyers market as much or more so than anytime since 2008 and might be heading into softer selling prices on a lot of our guns.