A: Obviously this depends on what somebody is willing to pay for it. Ebay, Craigslist, and Swap Meets are the common sales places.
Determining value is normally done this way
Common Tools: If your tool is one of many copies, there are sales all around. Watching these sales, and buying over a period of years, I have a feel for these. You can get the same feel I have by finding examples and noting the prices. There are variations over time.
Desirable Tools: If your tool is “desired” it has some value. Rarity alone does not mean a tool is valuable. Generally, the tools that still have a function (sockets, ratchets and wrenches) have a value. Generally tools in sets are more desired than a single tool. So an old 1950s socket set has value, a 1950 headlight beam focus tool does not. A Wrench that is a part of a common set is more valued that a special wrench for a sensor, or a specific car.
Rare Desirable Tools: This is what everybody hopes to find. The more valuable Snap on tools are pre WWII. World War Two flooded the market with tools. Even today, WWII era tools are common and not highly valued. Tools from the 1950s and 1960 often demand better prices. If there are very few examples and people want those few examples – that drives up value. Before WWII, and even more so, in the early 1920s Snap on was a very small company and made few tools. These have the most promise of collector value.
Large Socket Sets: These are the 5/8 inch drive, the 7/8 inch drive, the ¾, 1, 1 & ½ drive. These are a little different that the smaller socket sets common in garages. These were industrial and heavy duty sets. The 5/8 and 7/8 are orphans. They have a niche collector market, and not much else. The ¾, 1 and 1 & ½ inch drives are still used. The Orphan sizes are worth a $70 and up for the sets. I have purchased numerous sets for $100-200 is great shape – complete and extensive. The sets in sizes still in use can be resold into industrial use (purchased to use, not to collect). The buyers tend to be companies and tend to compare prices to new sets. These can bring $300- $2500 for nice sets.
Tool Boxes: There are 2 types: the small set boxes and the larger Chests and Roll Cabs. The small set boxes often are for socket sets. The early ones from the 1920 and 30s are often valued. The puller, reamer, and special set boxes are generally less valued that the socket set boxes. Plastic boxes are not – in my opinion – collector’s targets. On the Chests and Roll Cabs – The first 1920s examples have value, the K-60 is very desired because of its Art Deco curves. Other than these, the boxes are generally used for tool storage and not collected. There is a simple reason for this – they take space and they are heavy. So one can not sell and ship across the country – it costs too much. Once you have one, getting number 2, 3, 4 …10 takes a lot of space. Most people can find utility and space for one, or two sets, but 10 roll cabs? Not likely. So the market is local and it is in the $200 – $1000 range, with most roll cabs or stationary chests selling for $300 or $400.
Catalogs: Early catalogs are very pricey. Basically the price decreases as the catalog gets newer. Rare and odd ball catalogs from the 1920s and 1930s may have some real value, the 1940s and 1950s are ranging in the $60 area. A catalog for the 1960s or 1970s maybe $10-$24. Newer catalogs are very common. They can be worth $5 or $10.
Also, I will tell you what I think if you like – Email me a photo at f.murch@sbcglobal.net