A friend of mine is trying to put together a complete set of autographed 1968s (at least I think they are 1968s). Its something that I always wondered about -how does anyone chase down the gold insert sets, or the Target Red sets, or get a full autographed set?
Obviously money is a key player, but it is time and dedication well beyond opening pack after pack to collate a 2016 set.
I was amazed to discover you could collect *this autographed set:
http://www.sportsartifacts.com/aagpblcards.html
Impressive.
SABR's Baseball Cards Research Committee 
I have a friend who has a 1961 Topps set missing fewer than 10 autographs. I could ask him to write about this.
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During the 2001 All Star Game FanFest at Safeco Field (actually, it was held across the street), I got in line to have (then Seattle Mariners pitcher) Jamie Moyer sign his 1989 Topps card. While waiting in line, I was reading the Rickey Henderson autobiography. Quick read, usual stuff you would expect. When I got to Jamie, I placed the card in front of you him and remark: “This must take you back.” He picked up the card (he is depicted throwing off the mound for the Cubs) and looked at it carefully. He smiled and chuckled, as if he couldn’t believe he was ever that young, and replied, “Yeah, it does.” He gave me the signed card back, and noticed my book. He asked me what I was reading, and I told him. He asked what I thought of it, and I said, “Well, you know Rickey, he’s always the hero!” We shared a laugh and I moved on. Funny enough, Henderson came to the Mariners the following season.
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Does a ’55 Jackie Robinson autographed by Doris Kearns Goodwin count?
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You need to get lucky and not have cards in the set of players who won’t sign (see, e.g., Doug Flynn who wouldn’t sign his 1986 Topps card for 25 years and now only does for a $400 charitable contribution, or any of the folks listed here: http://spaamcollectorsforum.forumotion.com/t1846-athletes-and-the-items-they-won-t-sign ). And also not have anyone in the set who died before or soon after it is issued (e.g., Steve Olin’s and Tim Crews’s 1993 cards or Jose Fernandez’s cards this year). If you can avoid those, you might actually be able to complete a set signed.
(I’d personally rather have an unsignable card, like the Ken Hubbs In Memoriam card, than one that can be signed but only was a few times, like the Puddin’ Head Jones 1983 Phillies team issue postcard that he reportedly only signed a few of as it was issued in late summer and he died in September, I believe.)
As for collecting all the gold parallels, I have no idea, nor do I want to know!
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I was lucky to get Jim Bouton to sign the 1970 Seattle Pilots team card–which he is not on! He looked and I looked…and I figured out that it was taken when the Pilots briefly sent him down to the minors early in the season. He had never seen the card before, oddly enough, though he was never on a Topps card for the Pilots or the Astros in 1969 or 1970–as far as I know.
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