Cool thread...
The longest for me is easy...when I was 12 years old in 1982 I got my first 1969 Topps card. I loved it. Considering I was born in 1970 I LOVED the fact that I actually owned a card OLDER than me. I made up my mind right there that I would one day own the complete set.
I began to trade with anyone I could, and from 12 to 15 it was a tough go. I also begged my parents for the once or twice a year drives to the card shop a couple hours away. Once I could drive, card collecting subsided for a year or two...then I jumped back into it at 18 when my best friend at the time committed to the 1968 set. I dinked and dunked a card here, a small lot there...until I was finally down to 2 cards. On my honeymoon in Oregon we passed a Card shop in the middle of no where, and I finally found Dock Ellis (This was the highlight of that honeymoon, and quick marriage for that matter, easily! Haha). When I returned home, I looked up a card shop out of Boston, MA from the back of a Beckett, called them, and bought the final card over the phone...Jim Northrup. I had to mail him a check for $2, I remember it well. Very exciting day to get a card in the mail! I was 22 years old....so 10 years.
When the junk wax crash hit, I was totally out of the hobby. I got a call from a local collector in the mid 90's asking me if I had any vintage left to sell, and he offered me $500 for the set. I took it (he REALLY over paid, lol, most cards were P to FR) and regretted it the day it left my hands. After I remarried and started a family, I told my wife about my huge regret...she simply said..."do it again!". So I did. I started on the 69 set in 2007...had it complete a year later. That of course jumpstarted me back into the hobby (I routinely remind my wife it HER fault!
) A couple years ago I decided I wanted my 69 set to be EXNMT, I slowly began to upgrade. I am now the owner of 3 69 sets, and pondering upgrades that will lead to my 4th...
Edited to add - I TOTALLY remember my first Reggie Jackson RC card, outside the Mantle this card seemed impossible to a 12 year old in 1982, whose favorite player at the time happened to be Reggie. In 86 my parents moved to a new town where I quickly made a new group of friends, which was easy as I had been playing baseball against them for years. One of the kids had a slumber party and we were all told to bring our extra cards for a late night trading fest. Turns out I had the largest collection by far, and I was super popular as I had TONS of 84-86 rookies that these guys were dieing for. One kid shows up with a binder (rare then) with his favorite cards. All stuff from late 70s, early 80s...and low and behold, he had a Reggie RC, in EX shape or better. I couldn't believe I was actually SEEING one. Shocked, I wasn't even coy...I offered him whatever he wanted, I wasn't leaving that party without Reggie. He seemed shocked, laughed, told me he hated Reggie and that his dad gave him the card...told me an 85 Donruss Clemens and two 86 Donruss Conseco's would get the job done. I couldn't make the trade fast enough. I think I did everything but make a candle lit shrine to that Reggie card! For a year or two as those to mid 80s cards skyrocketed in value, I was the laughing stock of my buddies. It took a few years, haha, but I DID end up winning on that trade!