I've been working on a similar project for the better part of 20 years, and another member here, Ritchie, is also. Mrmopar is right on the money when he said the little known guys who played just a few games are the tough ones. Hodges, Stengel, easy to find, a little pricey but easy. The guidelines of your project also dictate how tough its going to be, IMO. I set out to get 1 signature from every Mets player on a baseball card. But I realized quickly that there were alot of guys who played a few games for the Mets but never appeared on a card in Mets uniform. So you make a custom or use a Wiz card. Then you have the issue of the guys who are deceased, who died before the Wiz set came out(Wiz set is huge, every Mets player up to 1991 on small paper cards), then you have to find a cut for your custom card, in just the right size to fit and authentic. And then you have to be cautious, there are scumbags out there who are selling fake sigs from rare, tough to find guys and it's easy to spend alot of money for a key piece of your project only to realize its a fraud.
I suspect 2 out of 3 Nino Espinosa signed cards on Ebay are fakes. I was lucky, I got him in person before he passed away and his "new" sigs don't match. Sammy Drake from the '62 Mets isn't easy. Neither is Sherman Jones from 1962. And Geremi Gonzalez from 2006, on a Mets card, is pretty tough, IMO. I'm sure Ritchie can add a few names to the list. How about Mike Bishop from 1983?