About $500. In 1964, the bean counters took over at Winchester so more attention was given to maximizing profits and less to providing a superior product. Two of the same model made a year apart will be of noticably different quality.
The biggest difference is that Winchester went from a controlled round feed(Mauser type) to a push pull feed(with out the mauser claw)type of feed action.this was done to cut the cost of production.This system is still in use today,but over time Winchester and other gun manufacturers have learned that there is still a great demand for the original controlled round feed of the mauser design.Especially with dangerous game chambered firearms.
From 1873 to 1964. U.S. quarters have the same weight of 6.25 grams.
You have 8 mints and 170 years worth of coins to pick from, so that's a wildly broad question. Pennies and nickels back to the 1940s are pretty much worth face value to a few cents more, assuming you found them in change. Dimes, quarters, halves, and dollars are worth at least 10 times face value just for their silver content. However, some can be worth much more as collectibles. You need to know the coins' specific dates and mint marks to be able to tell. The two sites linked below can be a big help. CoinFacts shows the location of mint marks for almost every U.S. coin ever made. Numismedia FMV lists the fair market value of U.S. coins by date, condition, and mint mark.