I suppose as an 'experienced' audiophile (and one who does not "guess" at what audio descriptors mean), I'd say that the biggest impediment to improving one's system is not the lack of good advice, there is plenty of it in these pages, nor is it a lack of vocabulary (the late J. Gordon Holt supplied an excellent basis for that decades ago...strange how newbies seem to complain about a lack of vocab, yet don't want to take the time to try and learn an existing one because it's apparently too hard??...really??...how do you expect to understand what you read?). But I'd say the biggest impediment is simply that the uninitiated are too hesitant to just jump in and get their feet wet and Try something based on that advice. The true complexity of this hobby is not to be underestimated and in it no ground can be gained without at least **some** amount of the direct experience of simple trial and error. Without any of that, relying on the sum total of theory and advice essentially becomes either useless or errant. Having been down this road before, I can tell you it's not advice that really make this hobby go round, it's experience, and there's generally only one way to get that.
Practically speaking, advice and recommendations can be very useful, of course, but can only take you so far. To answer the rest of your questions and settle remaining doubts, you will invariably reach the point where you must try something for yourself. Yes, that may cost you some bucks, large or small, but it takes a while for All of us to begin to feel confident about finding our way around in such a convoluted hobby. It took me 2 to 3 decades and that I suspect is typical.
Just remember to learn Everything you can from your mistakes...and that as you move forward in the hobby that those mistakes Will be inevitable, and that they are in fact a necessary part of the process. All the while, you are sharpening your audio instincts...instincts that, yes, may lead you to another mistake, but then that is the true nature of the beast, that's really how we learn and grow. The more practiced you are at it, the more reliable your audio instincts become. If I'm more confident now about my own instincts these days, I can tell you it's because I have the scars to back it up, lol!
But, that said, pure experience would not seem to be the best choice either; just randomly box swapping until there's a "eureka" may not be quite rational. But, either way, I'm saying that if you can't learn from your mistakes in this hobby, you may well end up paying for the same real estate many times over, and may God help you then, because IMO you will likely indeed have an even More expensive row to hoe from here on! If you think making the occasional buying mistake is an expensive proposition, just consider the alternatives!
Best of luck to all,
John
