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The pins that I use come from female header strips, and sell for about 0.90 USD for 3 pieces of 40 pin strips, including shipping. Example:http://www.ebay.com/itm/3-PCS-Strip-Tin-PCB-Female-IC-Breakable-40pin-Single-Row-Round-Header-Socket-New-/361872902978?hash=item54414e4b42:g:2wwAAOSw7hRWQCzj. I use my heat gun to soften the plastic, ad push the pins out from the tail side.
Using these pins eliminates all the need for special tooling, and they are cheap. In my early days in the Aerospace industry, we used eyelets to repair pulled out holes in plated through boards. There are some considerations to using them, and they were eventually banned from military systems, except under very special circumstances. It was found that over time, the solder joints between the pad and the eyelet would crack. This situation could be improved by using funnel head eyelets and flaring the backside. This allowed the solder to make a fillet with the underside of both top and bottom of the eyelet. Flaring the eyelet without breaking it was somewhat problematical. The tooling had to be just right, and the force sufficient to make sure that the eyelet was firmly swaged to the board, with no play.
The pins that I propose can be used in either of two ways. The solder tail can be stuck right into the hole, and the tail soldered first, with the top pad then soldered to the shank of the pin. The other way would be to make larger holes, if the pads permit it, and push the shank through the hole and solder it to the bottom pad, and the collar of the pin then soldered to the top pad. This does require that the top pads be a bit larger. The advantage to the second method is that the socket pins will sit flat on the board, and will always be in line without adjustment. This assumes that one can drill the socket holes in a straight line. Once in place. the solder tails can be broken off to get them out of the way.
I considered using these in the past but never actually bought some. I believe they are normally called pcb rivets or hollow grommets, or eyelets. Of all things, Walmart sells a bulk pack of 200 for $6.
Finding the right grommet setting tool could be a bit harder. A hand operated press with top and bottom dies will probably run over $100. If you have access to a small lathe it may be possible to make your own. Harbor Freight sells a watch case press that possibly be modified to either take you home made dies or machine the parts that come with it. If you still have to tools then getting more rivets/grommets/eyelets should be easy.
Mike