In the age of Bricklink and eBay, I suppose the story is becoming less frequent of adult fans of LEGO (AFOLs) who lusted over some set in their childhood or youth, but were never able to acquire it, either because of a lack of money or being born too late. However, I doubt this story is completely eradicated, because the great old sets, due to this very interest, command a high premium in the resale market, and most fans probably go through a "poor student" or "unemployed" phase or two. Certainly, I have.
I think I'm a fairly representative fan of my generation, in terms of which sets I always wanted but could never have (at least until Bricklink). I'm in my mid-twenties, born in the late '80s, and I started getting LEGO 18 years ago, at the Christmas of 1992. Despite getting a few more sets in the following years, it wasn't until 1996 that I really started buying sets for myself on a regular basis, and not until 1998 or so that I had the allowance/earnings to do so to an extent approximating that which I wanted. However, my very second set (mentioned before as "Dr. Freestyle's" Basic set) came with a 1992 catalogue, and I have memories of staring at 6086 Dungeon Master's Castle throughout the summer leading up to my first year of Grade 1. Although I lost that catalogue sometime around when I got my third set, said third set came with a catalogue (from 1993), which would forever dominate my imagination's definition of "the epic sets that got away."
Fans older than me have memories of the 1980s and first couple years of the 1990s, but while I have a few sets predating 1992, my systematic understanding of the LEGO System's history only went back to the 1993 catalogue, so Classic Space, Blacktron (1), the Black Seas Barracuda, El Dorado Fortress, and Black Falcons only existed on the barest fringes of my mind, until I discovered the Internet, ca. 2000-1, and was able to put some context to these very old memories. In the meantime, however, the 1992-3 releases captured my imagination, and because I could never have them (by the time I had money it was faaaaaar too late), they have always been "the ones that got away."
Now, while you might have asked my younger self to name some he wanted but could never have and he would probably have given you a set name, the reality is that it tended to be a whole theme that captured my imagination, and the largest set was simply a placeholder (a "synecdoche," to use the literary term) for the theme of which it was a part. This post will be the first to examine these long-cherished themes, and see why I loved them, and how well I've succeeded in acquiring them.
Perhaps the strongest such theme that I never had were the Imperial Guards, from the Pirates line. The Imperial Guards were released by LEGO in 1992 as a red-coated replacement or upgraded version of the blue-coated soldiers who had been the pirate's nemeses since the advent of the theme in 1989. Although the pirates were very much the darlings of any game my brother and I ever played--while ostensibly still the 'bad' guys--I always preferred the Imperial Guards, part of a long-held preference for those who uphold the law rather than break it.
Of all the sets I've ever wanted, but never been able to find/afford, none have ever captured my heart so well as 6277 Imperial Trading Post. That set had it all: a base, a ship, and a boat for the pirates. For that matter, it had both pirates and good guys--including a rare example of civilians in the crew of the little ship. Most importantly to my young self, it had four redcoats, including the elusive and much-wanted admiral figure.
However, I would have gladly settled for 6271 Imperial Flagship. Though it had no base and had no pirates, it still had three of those cherished redcoats--including the admiral--and was a larger ship than any I ever owned--although, come to think of it, had I got the Imperial Trading Post, the little ship there would have been the first (and so the largest) I owned. It was not until 1998 that I got a ship... assuming that one can dignify 6250 Crossbone Clipper with that title.
Meanwhile, back in the mid-1990s, the Imperial Guards had not one, but TWO beautiful larger sets that I desperately wanted... and never had. Even today, I still don't have either of them. I have some Imperial Guards, having acquired 6252 Sea Mates at the height of my Imperial Guards era. In early 1997, I also managed to buy the last Imperial Guards release, the 1995-released 6263 Imperial Outpost, which satisfied my need for an Admiral figure. Until the discovery of Bricklink, however, that would be all the Imperial Guards I would find.
Even today, however, given the high popularity that the redcoat figs have with both nostalgicists like myself and army-builders wanting Napoleonic-esque armies, I've only upped my numbers by one. Consequently, I was happy to see the 2009 release of a new Pirates theme, including an updated version of the redcoats--although it's worth noting that finances prevented me from doing more than amassing a collection of the smaller sets. Even so, my new-redcoat army is larger than my old-redcoat army.
I still want to get Imperial Trading Post and Imperial Flagship someday, but the prices on Bricklink are not encouraging. I would probably have to spend $150 for the former, and $80 for the latter (USD), and that's assuming the prices don't climb more by the time I'm in a job where I can consider such purchases. Until then, these will always be two of the biggest "fish" that got away.