I've sent out about 20 requests over the last two weeks and am hoping today's return is the start of a steady stream.
Bill Dailey responded to my request in just six days! I sent a 1963 Western Oil print as well as a 1963 Topps. I had enclosed a silver sharpie for him to use on the print, which he did.
I now have 11 signed prints from the 1963 Western Oil set. There are 24 prints in the set. I think the only living player that I don't yet have is Jim Kaat, so I'll have to hope I can find a lot of these already signed.