One of my favorite examples along these lines (other than the F-117 shootdown) is the Argentine Air Force during the Falklands. They did what no one in the Royal Navy (or the world for that matter) thought they could do with their obsolescing aircraft and weaponry, and that's sink a lot of British shipping. Would have been even worse, if the accounts I've read are correct, if they'd had the proper fuzes for the iron bombs they were hitting the ships with.
The F-117 got shot down because we got sloppy and overly reliant on the technology, rather than sound tactics. Furthermore, the same thing caused the death of around 150 Kosovar Albanians, in two separate incidents, when our FAC(A)s mis-identified refugee convoys as Serbian army formations trying to V-ID vehicles from extreme altitudes, relying on technology rather than sound tactics. Its also the reason why 17 Marines got killed in An Nasariya by USAF A-10s in March 2003. I could go on and on here. Bottom line, and this was my original point that kind of got lost in the discussion, is that its not the tools, but how you use them that make the difference.
We built something like 44,000 Sherman tanks during WWII. The Germans built something like 1,400 Tigers. I don't know how many T-34s the Russians built, but it was close to the Sherman numbers. Now, I've never heard a German tanker complain about the Tiger, much the opposite really. But, ultimately, that type of production and fielding disparity was decisive, rather than the quality of the weapons. If we can't afford to buy enough F-22/F-35 to persist in the air in a high-intensity environment, that's a problem in my opinion. The Osprey is another aircraft I have similar feelings about, but since we're getting them in quantities for a one-to-one swap for the Frog, I don't have as much heartburn about them. Its not about the length of development, or the cost of development, per se, but the ability of the aircraft to operate continuously in a high-threat environment during sustained operations. Are we gonna have enough of them after a few get shot down, some are lost due to non-combat operational losses, and after the wear and tear of high-intensity operational tempo starts to impact our ability to maintain them in sufficient numbers. Maybe we will, but my gut tells me that we're getting close to a point with these two aircraft where top technology is too expensive to be cost-effective.