Should I buy older, used chisels?
Depends. For newcomers it can be problematic, as you need good tools to use now but have not yet acquired the skills needed to rehabilitate abused antiques into something useful:
If you already have good grinding and honing skills and can also make handles, then flea markets and local and on-line tool auctions are an inexhaustible source of top-quality, high-carbon tools; often at prices less than you’d pay for the equivalent quantity of raw tool steel. Of course, you are trading your labor and rehabilitation skills for the money you save – and the labor can be considerable. I’ve done a bit of this at various auctions for myself and for tradesmen friends who don’t use computers, and I’ll share what I’ve learned.
As long as the chisel is old, factory-made, and intact with good length remaining, I’m not too concerned about condition short of severe pitting. For me, blade backs are easily ground on the belt sander to flatten and remove pits, sockets can be repaired, steel can be polished and blued to hide rust staining, and handles are easily made on the lathe. Anything marked "Stanley", "Witherby", "Winchester", “James Swan”, "Chas Buck" or "L&IJ White" is generally going to a collector for too high a price unless they are part of large, handleless lots. Older (not newer) Greenlee and Buck Bros, New Haven Edge Tool, Ohio Tool, Crossman, DR Barton, Underhill, Union Hardware, Jennings, Sargent, GI Mix, Shapleigh Hardware, Eric Anton Berg, Dickerson, Gillespie, Wye, Dixon, PS&W or PEXTO, Robt Duke, Fulton, Merrill, Butcher, Stiletto, Hibbard OVB, Simmons Keen Kutter, Lakeside and several other old makers and hardware store brands are every bit as good as the collector prizes and are much less expensive. Most unmarked chisels of that era were usually made by one of the above makers for a hardware distributor and are also generally excellent.
The only really poor socket chisels I've observed are newer Craftsman (older socket Craftsman were often made by Greenlee) of shiny, chrome-vanadium steel, some "Eclipse" brand and the occasional Stanley Defiance that refuse to take an excellent edge. Also, used tool dealers rarely know their wares well, and you have to look at each and every listing in detail to find what you need.
Having rehabbed around 200 of these old chisels and gouges over the past several years, I'll offer a quality opinion based on the ones I've used:
New Haven Edge gov't contracts marked "USA" or "USN"
Hard to Call between First and Second....but always most excellent:
PS&W or PEXTO
Greenlee thin paring chisels
New Haven Edge
Older Buck (older chisels will have sockets, which went out around the time forging did)
Older Craftsman made by Greenlee
Douglas (precurser company to Swan)
Eric Anton Berg
Shapleigh Hardware (Diamond Edge brand)
Third-Tier (Don't buy)
Newer Greenlee, Buck or Stanley socket chisels made in the 1960's and later.
Any chisel with a vanadium finish like used on today's mechanic's tools.
Al the hardware store brands were made by a larger chisel manufacturer. Greenlee seems to have made a lot of them. One store bought from Witherby....Shapleigh?...but I don't remember which one. Shapleigh bought Sargent planes as house brands, and may be the one whose chisels were made in Winsted, Conn.