Biggest regrets:
1) I was able to get a 1931 US Tour of Japan ball for a great price. The ball had a beautiful Lou Gehrig signature. A few years later, I sold the ball for a $1000 profit. I've sold many items I owned and find that I miss almost none of them. At the top of that short list is this one.
2) A few years back at the Atlantic City Nationals, a dealer randomly asked me if I wanted to buy a Gehrig signed photo. I think it was $2950 or so. It was a great looking piece. I'm not sure whether it was a Type I photo but it was obviously vintage. I passed instinctively as I was thrown off by someone randomly offering me an item. I'd love to have that one.
The positives remain to be seen. I bought a few items with eyes towards players making the Hall of Fame. Still waiting...