They quit making them because todays generation is buying AR15's. In other words, they don't sell. No profit, no factory, no new rifles. Now they are Japanese, an irony if there ever was one.
My Oct. '64 is a functional rifle, the finish pitted, and not getting any better. It seems that Winchester had to make the decision back then to 1) go out of business for lack of profit, or 2) stop putting in expensive hand labor and parts to increase the profit margins. They stayed in business, only the purists got their noses bent, and they have warped the market price ever since. If I can get mine for $175, and it shoots the same as one four years earlier, the deer certainly won't notice or care.
As a matter of money management, I certainly would buy the early model - for it's collector value, as an investment, to be sold in the future. It's utility value as a shooter, no. It's overpriced. Be aware of what it's bought for and treat it accordingly, no one much wants a pitted rusty pre-64, unless it was owned by a movie star or such. It's all about the grade of condition and provenance.