Con argues that perfect doesn't mean boring, but gives no support for this. Consider a finished puzzle. You are done. You have no more left to do. If someone gave you a finished puzzle, the only thing you can do is to mess it up and restart. Similarly, if your life goals are all accomplished, then your life is perfect and there is nothing else, no more stimulation, and hence, you would be bored. Con brings up giving himself more time to debate, but firstly, having infinite time to improve oneself can lead to procrastination and gives excuses to be lazy, as the argument "I can always do it tomorrow" would always be true, and hence you would likely stagnate and never improve. Keep in mind that your average human wants to take shortcuts and find and easy way through, that's why we think so many people are addicted to our phones and computers, as we are sucked into what we believe is "perfect" for us, but takes away from social interaction and actual life. If your life was so perfect, then you would likely be less productive to society as a whole. And wouldn't making yourself the best debater in the world instantly fix your problem of wanting to debate? (This, ironically negates the need for you to improve, which proves my point)
Now con brings up the possibility to help others improve their life as part of your perfect life. However, it requires a very generous person and being able to judge what is right and what is wrong. Most people are selfish and don't care about 7 billion people asking to have a perfect life. It would simply take too much of a mindset to be able to gather everyone together and mutually agree on a perfect society; with 7 billion different view points, a perfect world is far more impossible than the perfect life for yourself.
Finally, con admits that mistakes are crucial for life. That then brings a slippery slope, which mistakes are actually necessary and which are not? This becomes incredibly vague to define and hard to say which one you're willing to accept and which one you think would be merely a plot device to make your life more realistic. Consider hacking a game, you can easily defeat it and you can make it very easy. But almost all cases you should not do this; a game is meant to be fun and challenging. Being able to perfectly do everything easily means the game just becomes a relaxing breeze that loses its purpose and its challenge. How can con know for sure that the frustration caused by a small mistake won't deteriorate the "perfect life"? Con's case contradicts itself.