1)First and foremost, good luck in the quest. You might want to consider narcotics as a healthy alternative to this audio habit.
2)Do your research! Audiogon is a fantastic resource and there is no end to what you can learn from your fellow posters. Take a look in the virtual systems section and see what combinations folk have pieced together over the years and at what budget. This will give you a good idea of what you can get for best bang for the buck. Check out budget minded, ever evolving, opinions please- all of these are great places to learn from the mistakes of others. It also will have the added benefit of drawing your eye to good places to look for bargains as some brands or models will be represented over and over again with gushing reviews.
3)high end is really a relative term. Depending on who you talk to, the same system could be considered a starter or the last word in the true high end. Check out enjoythemusic.com. they usually have a couple of pieces on good sound for under $2k.
4)It is pretty hard to give blanket recommendations of one or two pieces from the thousands that are available. Some good suggestions have been posted here. Everyone has opinions and it is impossible to objectively evaluate subjective attributes of what sounds good. Rather than reading about sound, try to find a dealer, even if they are 50 or 100 miles away. Theres nothing like sitting in the room with gear and listening to equipment that will become your buddy over time.
5) To the extent that you can, as you build the system try not to make too many changes at once. For example, if you can avoid it dont add new interconnects and new speaker wire at the same time. Dont swap out cd players and speakers on the same day. That might seem strange, but to the degree that you can make changes one at a time, the resulting changes will be obvious. Because obvious changes are not always desirable, it is handy to know where the changes are coming from. True, there are major financial benefits to making changes slowly. But more important is the learning that you develop with more time to research gear and come to understand the strengths and weaknesses of your evolving system.
6)Dont forget to budget for cables! This is a subject of some controversy as zealots from various cable religions wage crusades upon each other. Theres some good material here on a-gon diminishing returns.
7)Used gear? Your mileage will vary. I tend to worry less about getting burned by total strangers, and more about being penny wise and pound foolish. For example, a used pre at $250 might seen like a great deal, until it develops a crackly pot that costs $125 to fix. As a rule, I try to avoid older used gear with motors.
8)The rules of consumer electronics dont apply. In that realm, for example, conventional wisdom says things like a) spend 50% of your budget on speakers, b) all cd players sound the same, c) rca cables dont make a difference. Those rules are rapidly overturned once you start playing around with this fancy stuff.
9) Consider vinyl. Though I will not join the debate about which format sounds better, I will argue that you can often find LPs for a fraction of the cost of cds. The money you spend on an analog front end (at some point) will easily be recouped in the savings from much lower software costs. This means that a pre-amp with a phono-stage is very desirable.
10)Be patient. Soon come.
