I go along with what most of what Bill has to offer. Unfortunately, the availability of “experienced” tools is greatly affected by the population density and the history of the area you are in. I try to hit the flea markets, hit antique stores and check out the Craigslist ads when I am in a given area. Some people buy T shirts and I bring home old tools, what can I say? What I have found is that areas of the country that didn’t have a lot of native forests and thin population densities never had many woodworking tools. Also, areas that had much of their development after the era of hand tool woodworking never saw many of the better quality tools. Much of the Northeast has been gleaned by collectors and dealers over the years and you don’t even see many tools in the antique stores there anymore unless they specialize in tools. The best offerings I have seen there are either with the speciality dealers or are in estate sales.
The areas of the country that still seem to have lots of tools are the middle sized towns of Appalacia and the farming areas of the mid-west, most noticeably Ohio and Indiana and Illinois. Another tool rich area is retirement communities in Florida where the retirees have located from other areas and brought their collections with them, Those are now showing up in estate sales and filter down to the markets sometimes.
You an also find offerings in areas that became craft centers during he 1970’s such as Seattle. A lot of those folks are getting up in years now and their treasures are being passed on.
I have tried posting “looking for” type ads with little success and some of the dealers have told me they will sometimes, but not often hear back on them. I think you would be better off getting together with local estate sales professionals and letting them know what you are interested in. I always look for estate sales and shop liquidation sales. A lot of folks selling several pieces of larger shop equipment will have hand tools available but they don’t advertise them because they don’t see them as big money items. It always pays to ask.
If you ever get to London in the UK try the southern end of Portobello Road market and Bermondsey market. I have been lucky there on a couple of occasions. There seems to be a lot of traditional tools in the UK and I would love to spend some more time there hitting the markets and boot sales. As a last resort, there is always EBay.