My experience from a selling standpoint has been that there are vintage photo collectors, and there are autograph collectors, and typically having a vintage photo signed will remove it from one camp of interest to the other. I don't see the two areas of interest merging much unless the signature is also vintage as in a nice fountain pen signature from the athlete's playing days. I don't usually see the autograph collectors paying a premium for a sharpie-signed vintage photo over what they would a sharpie-signed modern reprint of that same photo, but I have heard from plenty of photo collectors that they have no interest whatsoever in signed photos, regardless of how old the photo itself is.
That said though, it's really a matter of preference. If you're collecting autographs and prefer the look of a vintage photo signed by a player over a modern print signed by the same guy, then it's up to you whether it's worth spending the extra dough for that vintage original photo. Something else to consider would be having a modern reprint of the vintage photo made for signing while keeping the original "unmarred".
Personally, I would liken it to collecting player autographs on $20 bills vs. collecting autographs on $100 bills. Sure, the signed $100 bill will be more desirable, but is it worth spending 5x as much for the material upgrade? Just my 2 cents...
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