I've never attempted to mail anything to a former player for an autograph. I figured this was worth a shot. Included cash in the envelope based on what I've read in these comments.
My dad and I met Jim Rice at a Worcester Sox game in June 2024. I printed out the picture we had taken and mailed it to Jim with $30. I received the picture back, signed. I sent it out on October 23 and got in back in the mail on October 31. I was pleasantly surprised to get it back so quickly! (I only live 2 hours from him but still I thought it was a quick turnaround). It's going to be a good xmas gift to my dad.