What a good question and one I have been struggling with also. I've been on the upgrade path for the last few months and after going around to my local hi-fi shops have decided that for me the best way to learn is to treat places like audiogon as almost a lending library. I research what I think I'm looking for, read the massive amount on here and elsewhere and try and dial in the sound I'm looking for within my budget. Then try and find that sound. Audition that item in my house for awhile and see if I want to live with that sound or keep hunting.
The best I got from the hi-fi stores is to learn what sound I don't like. I like the suggestion of an audio club, I did not know that existed, but I will be looking into that.
I also think it's really tough to match your house acoustics, I live in a house built in 1799, and my equipment is in the old part of the house. The pros are extremely thick walls that seem to have a nice affect on the sound, but the room is the oddest shape and I have a wood stove somewhat blocking the whole sound. But, again, buy getting the equipment in my house, I can hear exactly how it reacts to my particular setup.
The best I got from the hi-fi stores is to learn what sound I don't like. I like the suggestion of an audio club, I did not know that existed, but I will be looking into that.
I also think it's really tough to match your house acoustics, I live in a house built in 1799, and my equipment is in the old part of the house. The pros are extremely thick walls that seem to have a nice affect on the sound, but the room is the oddest shape and I have a wood stove somewhat blocking the whole sound. But, again, buy getting the equipment in my house, I can hear exactly how it reacts to my particular setup.