I paid $79.95 for a brand new, in the box, Sears-Roebuck double 12 gauge. 30" full and modified chokes, hardwood stock, twin triggers back in 1967 I guess it was. My mother ordered it out of the Sears Catalog, and a Sears truck delivered it to the door, along with a brown hunting coat, and two boxes of Sears shells.
Yea that was a lot of money to a 15 year old kid on those days, but I like being able to tell about ordering a gun from a catalog and having it delivered in those days before GCA-68. That was quite a deal when you think about it.
Best deal recently was a Harrington & Richardson 999 Sportsman. I spotted it in the back of the case at my favorite dealer. They had it tagged at $179.00 which I thought was a pretty good price. I offered $150.00 and they took it. As we were writing up the papers, I notice the rear sight was missing (somewhat common for these I'm told). I pointed it out and said "That should be worth another $20.00 off." The clerk said "Ok". So I got it for $138.00 OTD.
One of these days I'll order a sight for it.