I started collecting in 1991. Sometime in 1992 I got my first price guide. At the time, my most valuable card in my collection was the 1992 Topps Brien Taylor:
At the time he was a hot rookie and this card was $3 book value. For comparison, Nolan Ryan was $1 book value. This card is now a common and pretty much worthless.
For about a year or so after that, it was my most valuable card. Some time later I got a few different $5 cards, but none that I remember specifically.
The next card that I can recall as being my most valuable was a 1993 Fleer Ultra Ken Griffey Jr All Star, which at the time was $15 and was the most valuable card of my collection. I don't remember how I got it, but i think t was in one of those variety blister packs sold at walmart type stores.
This card is now worthabout $6 according to ebay auction closing prices.
The next card in my collection to become most valuable was the 1992 Donruss Update Kenny Lofton:
]img]http://i.ebayimg.com/00/s/MTEwNVg4MTU=/z/ibEAAOxyRhBS5dmC/$_12.JPG[/img]
I acquired this card through a 1992 Donruss factory set. Each set has 8 or so Update cards included as a bonus. Back in 1994 or so Kenny Lofton was hot, and this card was worth $40 when I first got it, and as I recall once worth at a maximum of $80. The above image is from an ebay auction that was Buy-It-Now at $2.00 and didn't sell.
The next card to get the crown was a 1996 Topps Chrome Refractor Roger Clemens.
I pulled it out of a pack I got out of a grocery store checkout isle. I remember being ecstatic and telling my mom "I got a refractor" and she having no idea what I was talking about. At the time it's book value was $60. Now you can get one on ebay for about $15.
Then I stopped collecting some time around 1997. I recently started back up, but I have yet to attain a card worth more than $60.