I have always liked items of pro players that are from before they were pros, during barnstorming tours, or playing with local teams during or after their careers. Let's see your items that fall into these categories. I think I recall a few neat Ty Cobb items like this, hopefully one will make an appearance.
I'll start with a RPPC of Cy Young playing with the local team in Ravenna Ohio just after he retired. Cy last pitched in the majors in 1911, but in 1912:
Cy Young went South with Boston in the Spring of 1912 and pitched well in Regular vs. Yanigan games and in exhibitions. He was with the club when the season opened, but never played in a game during April and into May, and his name seldom appeared in the papers. On May 19, 1912 it was reported in the papers that he might pitch the next day in Pittsburgh where he had been successful in the past, but he didn't appear in the game. Finally it all ended on May 24 when the papers carried the story that Cy Young was retiring from baseball. The decision, he said, was his. The club's management said they wanted him to remain as a player.
from: http://research.sabr.org/journals/cy-youngs-final-fling
On September 2, 1912 he donned his Red Sox uniform to pitch for the Ravenna team.