Complete newbie needing guidance/purchase advice

Hi folks-

First of all, let me apologize in advance for a lengthy post. I'm a brand new forum member after recently being introduced to this site by an acquaintance who heard I was looking for sound advice... As my thread title states, I'm completely ignorant when it comes to the audiophile world, but I really want to start building a system and learn something in the process. A little background on me: I've been making a living as a recording artist and studio musician for almost 20 years, but my career choice as a music-maker has somehow ironically detached me from the simple pleasure of just sitting and _listening_ to music for the sheer enjoyment of it. My wife and I are currently in the process of remodeling our bonus room into a media room, and one of my objectives is to at the very least turn it into a space where I can do some critical listening.

I currently don't have anything decent... Just some old Bose bookshelf speakers and a Yamaha surround receiver. The closest thing to 'something decent' that I own are a pair of Etymotic ER-4S headphones coupled with a Headroom headphone amplifier.

The big limiting factor is my budget. Given that fact, maybe I have no business posting here... I will probably need to build this piece-by-piece over time, so I'm content with having to stretch the process out. I'm not concerned with having to have the 'best' of anything; I would just really like to make listening to music an engaging and emotional experience for me like it was for me many years ago.

Would a speaker purchase be a good place to start? I was perusing the Audiogon classifieds today and saw that there is actually a pair of DK Designs LSA-2's for sale local to me. The asking price is at the top of my speaker budget, a little over a grand, which I realize is probably 'chump change' in the audiophile world. However, I've read some reviews and they seem mostly positive. Would be super-convenient to be able to find something nice that was used and local, but as I said before, I'm completely new to this. Another related question: Is it better to go with floor-standing speakers, or can decent sound also be accomplished with bookshelf speakers combined with a subwoofer?

Also, what are the other 'basic' components that would need to be purchased? The only other thing I know I'd love to have would be a decent turntable; I'd love to be able to go and purchase some of my favorite classic albums to listen to once again. Do I need a separate preamp and power amp combination? Are there any 'receivers' that do a decent job of covering both tasks?

Any other feedback or direction you experts could throw my way would be greatly appreciated... Thanks in advance!