What a tortuous thread. Not sure why we do this to ourselves but I want to join in the communal pain.
For me, it's been Huge Altecs. Oh my. How many? So many. A pair of model 19s for $150. Why? Well, the wire going to the woofer was broken. And they were so big.
A pair of A7 VOTT for $600. Happened across them right before we were moving across the country and already had an entire household of stuff that would prove a tough project to fit into the truck. Geez. They were the same size as a washer and dryer set...
Then, in St. Lous, more pairs of VOTTs. At $1000 or 1500/pair. Monstrous things.
Then more recently, a minty-looking pair of Altec Valencias, with that impossible-to-replace fascia in perfect condition. $2,600/pair. Why didn't I pull the trigger? Too much of a side-grade from my current JBL 4430s. Oh well.
The biggest ones I ever let go of? That is, I didn't miss out on them, I decided to advise the buyer I would not proceed with my purchase. A pair of JBL 4355s. Yes. The unobtaniums. For the extremely reasonable price of about $6,000. Yes, if you see them for sale they're typically about $15,000. The seller even had a guy who would re-do the veneers for $600. They would have required bi-amping and would have really been too big for my listening room. But oh, they would have been fun. I considered buying and flipping them but didn't feel that was ethical, in this situation, as the seller already had a standing offer of over $10,000.