I agree with everything you said. It was too bad Agassi did not have the same focus in 96-98, or even 91-93 to what he had from 99-2005 at a more advanced age. He did have a sometimes chaotic relationship with Bolliteiri, IMO one of the most overrated coaches in tennis history early in his career, the discouragement after that crushing U.S Open final loss to Sampras in 95 (pretty clearly his most dissapointing loss ever), and the Brooke factor was a big one too I believe especialy after reading his Dad's book recently. It is interesting to wonder what if he were with Gilbert from the start instead of Bolliteiri who did not focus on making Agassi a smarter and fitter player which was what he needed since those arent areas of his expertise to begin, only focused on the ball bashing that Agassi was already outstanding at. I think that would have made a huge difference. Also if he were with Steffi Graf earlier instead of Brooke, LOL, ok I wont go there.
The 95 U.S Open final loss was really a watershed moment in his career though. Had he won that I almost gaurantee two things. One he would be alot more respected by people on this forum, no matter what else he did he would have clearly been the defacto slam dunk #1 for 1995, 2 slams to Pete's 1, beaten Pete in slam finals, doing that in Sampras's prime would have elevated him to a whole new level of respect already. Secondly it would have made a big difference in his 96-98 performance I believe. As I said I think that was his most heartbreaking loss ever. The guy had an amazing summer, totally dominating with 4 or 5 tournament wins a row, unbeaten that summer. He was playing his best tennis ever, in the best condition of his life. He at that point had never won 2 slams in the same year or ended a year #1 so to do both for the first time would have been huge for him. To lose that final was just something he took a long time to get over I believe.
I would also suggest had he won a 2nd French or/and a 2nd Wimbledon it would elevate him higher in peoples minds, and that was very possible but unfortunately for him never quite happened. He was heavily favored to win that 1990 French Open final with Gomez but came out flat, and Gomez knowing it was a now or never shot for him with his nemisis Lendl skipping the event and at 30 years old played the match of his life that day and pretty much outplayed and dominated a flat and tenative Agassi. Then that 91 final with his soon to be nemisis Courier, he was up 2 sets to 1 and then the rain delay. I believe even Courier mentioned he believes he would have lost without the rain delay as his coach instructed him to make a tactical change in the final 2 sets which wouldnt have happened otherwise. Of course the tactically clueless Bolleteiri mentions in his book he regrets not instructing Agassi to make the same adjustment, LOL! Had he won either of those 2 finals it would have been huge for his career. As for Wimbledon his best great shot to win a 2nd Wimbledon was 2001. He was in the semis with a way past his prime Ivanisevic (who Agassi had upset in the 92 final many years earlier), Henman, and Rafter. It was pretty wide open for any of those 4 to win that year, there wasnt a clear favorite considering it was grass, and in the aftermath after two thrilling semis and a thrilling final each of the 3 who didnt win are probably still wondering what could have been, especialy Henman and Rafter who never won Wimbledon. Still Agassi had to like his chances of winning a 2nd Wimbledon at long last. He lost that amazing 5 setter to Rafter though, had a break point for a 2nd break lead in the 5th set but couldnt convert. That was a rough loss for him, and definitely a golden chance to win a 2nd Wimbledon with Sampras out. Had he won that it also would have made a big difference to how his career looks today.