For me the most frustrating was Colt. Colt was always behind the times. When I was shooting IPSC, which was before Springfield Armory or Kimber, Colt M1911's were the only game in town. AMT was in business, but their 1911 was so bad, shooters used to say
put enough Colt parts in it and it will work The thing was, the Colt M1911's you bought over the counter, you immediate sent to a gunsmith for basic stuff. Like beveling the throat, beavertail, Bomar adjustable rear sights, magazine well ported. You could add aftermarket extended safeties and mag releases. When Kimber introduced their Custom Classic, which was tight, did not rattle, and had all the features that you paid hundreds to gunsmiths to install on a Colt, I gotta say, Colt was doomed, and Colt was oblivious.
Colt was non responsive to the Market, by the time they did something, like lower the ejection port, the need had been identified a decade before. I remember the one and only time I saw Colt at the National Matches. They had a table full of AR15's with 1:9 twist barrels. I asked why they did not have any 1:8 twist and was talked to a Colt Executive behind the table. He had a very insulting attitude and let me know how little I knew. I was told, in so many words, they knew best because they were selling so many AR's on the commercial market. He and the rest of Colt were idiots. They came to the National Matches and not one of their rifles could be used in the competition with any reasonable chance of success. The 1:9 twist barrel was fine for 69's, but would not function with 75's or 80's at 600 yards. The 69 grain bullet was outstanding out to 300 yards, but was too wind sensitive at 600 yards.
Winchester did poorly and went bust. They are a brand today. They are still behind the market. I called about a decade ago, asking why they only had five round magazines to their FN PBR rifles, because I wanted a ten round magazine to use in across the course. I wanted to use a M70 PBR with a box magazine for the mandatory reload. The idea of a ten round magazine had been submitted to high management, but not implemented. You can look now at that market, a number of bolt action rifles have taken over the precision market, and a ten round magazine is getting to be a standard. Winchester still has not done anything to offer a precision long range rifle built around the M70 action. While I love the M70, Winchester is stuck back in 1937.