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#1
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I once thought along the same lines but signed programs are not highly valued in the marketplace. I was at a show at Shea Stadium in about 1977 and a treasure trove of autographed items from a sportswriter walked in and was auctioned off. There were maybe 8 or 10 Lou Gehrig items and they sold right around $100 apiece mostly signed photos including a large 16x20 photo of him in cowboy attire from rawhide (I think that was highest selling item at $150) . I saw a 1939 World series program with a beautiful Gehrig signature and most of the Yankees and Reds as well. first bid was 10 bucks and I was second bidder at $100 and won it. I sold it in 2006 and a few months before a 32 program with Ruth and Gehrig sold for just under 3 grand and my program sold for about the same. I think a big reason is that they are almost impossible to display. The main reason I sold it was because although I thought it was an amazing piece of baseball history I only handled it maybe 5 or 6 times in 30 years. So Yes a 27 signed program would be an amazing item a ball or photo I believe would sell for more.
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#2
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There is a signed photo page from a 1926 WS program in the Lou Gehrig scrapbooks at the BBHoF Library. (I had the privilege of examining them a number of years ago.) Gehrig had it signed in the same bold black ink by every member, and he signed it himself, as well.
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