-----
If we are talking 1/2" pitch a simple way to check/measure chain "stretch" is to meausre a length of chain consisting of twenty-five pins. A new chain will measure twelve inches. However much longer it may be than twelve inches gives and indication of its wear ("stretch").
Old chains and cogs have a tendency to wear in together so that they can be fairly worn and still not skip. However, when one matches new to old a skipping can ensue...
-----
I know this is an old thread. I feel it's an important, often overlooked subject that needs to be discussed.
Juvela, and Monkeyarms have both "hit the nail on the head" above with their accurate advice.
Chains wear and stretch; they stretch a lot! This stretch goes unnoticed when the wear on the chain matches the wear on both sprocket and chainring.
Many of us (me included) assemble our rides from many different part sources. Even on a bike that we got all assembled, we might need to make a gear change to allow easy riding. If you install a "like new" rear sprocket and use the used chain that was on the bicycle you stand the chance of having an incompatible combination of parts. Just because all of the parts are 1/2 by 1/8, or 3/16 by 1" is not enough to provide a smooth working drive system. Take the few minutes to actually measure your chain wear and keep the worn parts with the worn parts, don't try to mix new parts with worn parts. It's easy to measure even if you don't have a Park chain wear gauge.
I'm surprised that you guys spend hundreds of dollars buying used chains and not ask the important question HOW MUCH STRETCH does the chain have? This information should be included in the for-sale ad description, IMO. If the chain is NOS, or like new in 'pin to pin' length it should sell for more money. The "worn out" chains are good only for a "wall hanger bike". Please know the difference.
At our shop, we had two chains hanging next to the service write up desk. One was worn, as in very worn! The other was a brand new Sedis chain. They were 1" different in total length, hard to believe that the bike would still be rideable, and shift.
John