Chris,
With a piece like yours, that has so much value already, I would say the less you have to send it out, the better. If you can afford the money, go for it.
If you're not in a position to spend the money right now then I would go with older and more difficult guys first and then send away or travel to shows where multiple players you need are appearing together.
While they are all greats, I doubt that your poster would be that much less valuable because any one of those listed wasn't on it. Certainly not enough for me to risk sending it out over and over just to get a guy like Ozzie Smith on it. I mean no offense to Oz, but he sig is common and not likely to add much, probably not even the cost of the signature, to the value of the poster.
Value to cost ratios aside, the completist in me probably wouldn't be happy without all of them on it.
Good Luck,
Mark
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