Shadow - wow - what an in depth question asker you are! How old are you? I am curious whether you're old enough to have analyzed your personality - because I bet I could peg what it is after reading a question like this. Let me take a shot:
1. Conformation is probably the most important in showing in Halter classes - because halter classes are intended to show horses for judgement of their physical aptitude to perform. However, conformation is also important in the other show classes because if a horse isn't put together as well as possible, they won't move as gracefully or correctly as one that is. Conformation is basically the bunch of descriptions meant to communicate how well the horse is built physically. Further, I feel conformation IS always important throughout all aspects - when one sells or buys a horse, it plays into the value of the horse; when trying to determine what disciplines the horse will excel in conformation matters, when trying to find out why a horse is injured or not performing well, conformation plays a role.
2. I would disagree with your statement of item 2 because, as I said above - a better put-together horse (ie, one with good conformation) will naturally be a more graceful (ie pretty/cute) mover than one that is not put together as well.
2. That second question really seems to be a two-part question regarding people's response in this audience to how critical people are perceived. Remember, that we here attempting to answer questions, read only the information given. We must, from reading the grammer, spelling, typographical accuracy and our own ideas about how people of different ages and abilities speak and type try to figure out the age and aptitude of the asker as well as that person's experience level in the subject (here, horses). People don't naturally like to hear - and they don't like to see - others overly criticize anything. If you're going to criticize, it should be done with a purpose and iwth the right attitude, not an un-educated opinion. To say "you're horse is too heavy in the neck" would likely be viewed at totally critical and even damaging to say bluntly. but to say "your horse has an awfully heavy neck, which may not be a good asset for xxx (say barrel racing) but might be viewed as positive in XXX(perhaps a halter class)." You must remember that every opinion everyone has it tainted by their own experiences and their own ideas. You might ask me to judge the conformation of your horse- and if I'm smart, before I do, I'll ask what discipline you intend for the horse - because one conformational consideration may be OK for barrel racing, but not for dressage. Get my meaning here?
3. For your third question, I feel the statement you make is too general. I believe what you need to understand about horses (and many other things) is that each individual person and horse's situation is different. I would disagree with what you say if I'm finding a horse for an inexperienced middle-aged person or even a young person. A horse matures physically between 3 and 5 - they have mental maturity really about 6-8. Therefore, a 12 year old horse isn't really all that old since that's about half their natural age - they have a lot of years in them - I would purchase a 12 year old, very well broken horse for an inexperienced person well before I'd purchase a young horse of age 3 or 4 even if that young horse is well started. Between birth and about 5, it's VERY easy to affect a horse's training - and inexperienced person can take a horse of this type and ruin it if they are not knowledgeable about properly interacting with it. Really and inexperienced person can "wreck" an older horse - but the better trained older horses are less likely to be changed in what they know already than younger ones.
Now, if I were a trainer who was in desire of starting a young horse my own way, your statement might be true.
I know, from my 40+ years experience with horses and horse people that many people THINK they can breed a good horse, start with a clean slate and end up with a better horse than any they can purchase. But if they haven't either the loads of money to have the foal trained and started and themselves properly trained and started, too many things can happen that will make the horse unlikely to turn out as well as they think. There's an awful lot of horses out there who were bred by people just like this - they develop a small deficiency - usually in behavior or attitude that the owner doesn't understand so can't correct. That little deficiency grows into a large behavioral problem.
With all that said, it is easier to start a horse properly if you have the technical ability than it is to correct an already formed bad habit. But if you are not a professional in experience and knowledge, and you haven't the benefit or working with one during the process of starting a youngster, you are not likely to turn out a well-trained horse - thereby ensuring it gets the absolute best life it can get.
The natural horsemanship revolution being experienced in this country right now, I feel is pretty great. The premise is understanding how another species communicates and interacts with each other - something rarely done to this extent with other species in our world - if a person can do this well, they naturally will learn to interact with other humans on a much higher level. As more people gain more knowledge and accept more information as true about natural horsemanship ideas and methods, the abilitiy of the general horseowner to correct bad habits and build good ones will increase as well.
4. I have not idea where you get the 2 out of 20 information - and I am having a hard time figuring out whether this is a slam or not. Personally, for every answer I give on this forum, I could probably find hundreds of links to webpages that back it up, but I don't have the luxury of that time usually. I refrain from answering questions that are discipline specific in those that I am not familiar with - like dressage - ask a question about dressage and I won't answer it because I know little about dressage technically.
In my years of management I have learned that different people want to give and recieve inforamtion differently. You've probably surmised that I'm a very detailed person - I can't answer a general statement usually about horses with a general answer - because it really does depend. You can take 6 horses with the same problem and 6 owners and the solution to all 6 may be slightly different - bits, gear, tack and training all contribute to a problem. Each horse is an individual, each person is an individual, each pair of horse person, is something unique becuase each party learns differently.
some people in this forum want to give short, easy answers, but quite often the best answers are not short general ones unless the question is a yes/no question. I find that people generally ask questions that leave out and important part - so I must answer with if/then to give them the proper answer because I haven't the luxury of speaking face to face or back and forth.
Finally, you state in your question that your goal is to become a better answerer - to get more "best answers" from this forum. The people who get best answers are the ones with knowledge from experience. So the best way to get best answers is to experience. And in my experience, the best way to get experience is to ask A LOT of questions, keep an open mind and try lots of different things. It's as simple as when someone walks into the tack store and asks me "what's the best product for ......" (fill in problem here - dry skin, nervous horse, etc). there are TONS of products - do they want the one with the most natural ingredients, do they want the cheapest one or the one the pros use? Each person has a goal that fits one of these descriptions and we have multiple solutions. A good horseperson cannot be too judgemental or opinionated - a good horseperson knows there's more than one way to solve a problem - and the solution is based on many factors. Finally, a good horseperson is willing to listen to many different solutions and find the best one for them - they further are not the type of person who thinks "if you ask my opinion, you better do what I say or you're wrong" because we are not all alike with the same means and wants.
Sorry this is so long, but I hope it helps you. If you feel you need to learn more about horses - get knowledge any way you can. Get to expos and listen to all the speakers and clinicians you can. Buy books and read them all - learn what each prominent popular horseman is about now - rent DVDs if possible or purchase them. In Barrel racing, for example, one cannot go buy one book or one video by one author and become a pro overnight. You will learn something, if you go about it properly, from every single interaction with a horse, horseperson and non-horse-person you interact with. Take it all in, analyze it like you are now and learn from it all - pack it away in your brain for reference.
Above all - have fun!