I can somewhat understand your pain. I was fortunate to be able to purchase some '89s and '90s when they came ashore, along with occasional older vintages. But, funds were limited, and I tried my best (since I was in my Parker years) to maximize points with the funds I had. Therefore, I didn't buy that many Duhart Milons, Bahans Haut Brions, Meyneys, etc. All of which would be at (or, nearly at) prime-time drinking. And, those that I did purchase of these 'lesser bottlings' from '89s or '90s, I blew through in their youth as I didn't have other 'bargain' Bordeaux that were ready to drink (but, while youthful, they were still soooo gooood).
Also went through most of the older ones, with (seemingly) much more success than your older wine purchases. Even wines from vintages like the occasional '75 or '78 were successful (Grand-Puy-Lacoste one excellent example of those vintages, and I still remember tasty bottles of '75 Rausan Gassies for $35!). But, a lot of the older Bordeaux I bought then were meant for the occasional family gatherings or dinner gatherings when you wanted to pull something 'nice' out of the cellar that others were unlikely to have. And, of course, the nicer '89s and '90s were not at all ready.
But, then came the '91s. '92s. '93s and to some extent the '94s. I did not purchase. And, when the '95s and '96s came out, I didn't have as much to spend, and their prices were escalating, so I didn't buy. Same with '97 (well, same as in not much cash, and the vintage wasn't highly spoken of). Then the right bank '98s with their price increases. Once the 2000s were hyped, I dipped my toe for a few bottles, and I bargain searched for some '99s. Not a lot mind you. At the same time, I was also hopping onto the 2001 German Riesling train (mainly because of a local dumping deal here at the time of some very tasty '89 JJ Prum Kabs and Spats that were/are marvelous - and having access to one of Rudi Wiest's sales reps).
I hope to find some "deals" with '01 and especially '04 which I hope will be completely overlooked in the stompede for the '05s.
Anyway, I don't drink as much as you probably do (or, as most who post here regularly). So, I can tolerate the occasional '99 Bernadotte or Bahans (heck, even Domaine de Chevalier) when I want a Bordeaux, therefore keeping my hands off one of my prized older bottles.
Getting back to older wines, you just need to get on lists with some retailers who seem to do good work in this area. I've had great luck with the Premier Cru folks in CA with older Bordeaux. Unfortunately, they don't always have/find mid-level Bordeaux, but wines like '70 Ducru Beaucaillou, Montrose and Palmer have been wonderful (and, they at one time had them discounted to the point I just had to get some). And, I've gotten bottles in the past from the Chicago Wine Co auction guys (but haven't purchased recently through them). I know there are other retailers who work the world looking for properly stored older Bordeaux (I've kinda been out of the game of recent, but perhaps others can make provide sources).
But, if I had some handy cash, I'd probably spend 50% on new vintages, and the rest looking for "deals" at some of the auction houses from vintages like '78, '79, '83 and especially '88 (wouldn't overlook wines from other vintages, but these were the "not particularly hyped" vintages that still produced complete wines (at least with a majority of those I've been fortunate to taste) and wines that should be nearing if not already at maturity).
I also meant to jump in to your '66 Bordeaux thread, as this was my birth year, and I've had some worthwhile bottles over time. One of the first that I bought was '66 Lascombes - back in '91 or so. A very nice, nuanced and tasty wine that got some Parker points, but not a boatload. Next was '66 Leoville las Cases, another very good wine that I lucked out with. I've also had wondrous bottles with Palmer on several occasions (it was the first fairly expensive 'treat' purchase I made). Recent bottles of '66 Montrose have been quite alive but a bit austere. And, I recall having a Margaux once that was ok, but not what it could/should have been (at least not the height that Palmer is).
Anyway, there are lots of Bordeaux out there to be had and drunk. In a perfect world, we'd all have lots of cash to be able to have put down cases and cases of Bordeaux from the mid-80s at all levels (from non-classified to the Latours and Petrus). But, that isn't the case for most of us Bordeaux lovers. But that said, there is still plenty of bottles to chase that don't always cost into three digits.
Thanks for allowing me to get that out of my system.