Fun thread! I don't have this kind of history with audio, but it's a cool read. I've always been a bigtime movie guy, but haven't learned to understand and appreciate audio until recent years.
If you want a laugh, here's my progression as best as I can remember it. I've only just ordered my first set of "real" speakers. Judging from this thread I'm in for an expensive and obsessive habit.
1) Advent of the CD...so 1980-something. Realistic stereo system with "tower" speakers covered in ridiculous foam grills (so I have no idea about the drivers) that felt like empty cardboard boxes (and sounded about as good). These are the kind of speakers that come with a receiver that includes an equilizer where pairs of the sliders move together...but it *looks* like you can adjust a bunch of frequencies. The amp even felt like an empty cardboard box.
2) Zenith Allegro 2000's. I have no idea where these (I think) 1970's hand me downs came from. They were free, and they sounded more like a real speaker than the Realistic toys.
3) 5.1 system based on laserdisc and Dolby ProLogic (all Pioneer sources). A 12" downward firing sub and a center both by Olympus, I think. Little bookshelf type monitors by some other goofy company. Purchased at Radio Shack of all places when no one knew a thing about this stuff in general. But whoa! The sound is like...around you! Move out of that house.
4) New place, Sony 5.1 HTiB complete with a set of 5 tiny "plasticubes" and a tiny front-firing "subwoofer" if you can call it that. But again, whoa, now it's discrere!
5) Aquired two Hsu STF-2 subwoofers for a grand total of $300 in an amazing couldn't-pass-it bargain. I learn what a sub is really supposed to sound like and realize fully how incredibly terrible everything else I have is. Shakers go in to support the subs at really low frequencies. The effect is sweet.
6) A friend donates a pair of Sony bookshelves. Two plasticubes get replaced. Tonal match is nightmarish, but at this point it's just funny to try it.
7) Same friend donates a horrendous (but LOUD, hehe) pair of HUGE honkin' Fischers with enormous woofers. I stick them in as mains because at this point the absurdity is amusing.
8) Return of the Zenith Allegro's. I stick one in as a center...and holy cow at least I can hear dialog. Tonal mismatch across the entire soundstage is earsplittingly bad. This is an audio frankenstien monster from hell.
9) Upgrade to a 7.1 receiver while searching for "real" speakers. Displaced Sony platicubes find a new home as a back pair.
10) Ordered a full 7.1 set of Ascends. CMT-340SE's across the front, HTM-200's in the back. Looking forward to finally really having speakers. I'm sure the difference is going to be nothing short of staggering.
Step 11 is get some walls up in that basement, which has been in "prototype" mode for far too long. At least now I'll have something worthy of being somewhere other than in a storage cellar.