I actually do this all the time Scott. Years ago my dad found a large collection of used postcards in the basement of a "handyman special" he bought, most from the 30's-40's. I have all the cards sorted out by town, most of them local and if I go to the town I'll bring the postcard with me and put it in the mailbox if I can find the address. Much easier now with GPS. I've gone a little out of my way to deliver on the same date as the postmark before too so the people can say they got it EXACTLY xx years later
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Please check out my books on baseball history. They include the bio of star second baseman Dots Miller. A book featuring 20 Moonlight Graham players who got into just one game. Another with 13 players who were with the Pittsburgh Pirates during the regular season, but never played a game. There's also one about 27 baseball families, as well as a day-by-day look at the worst team in Pittsburgh Pirates history. All five can be found here: https://www.amazon.com/stores/John-D...hor/B0DH87Q2DS
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