Used vs New vs Vintage vs Floorstanding vs Bookshelf vs ..... OMG!

tykozen,
millercarbon gives you good advice, and I think the most important thing that he said is listen.

A lot of well meaning writers and salespeople and people that you speak to will have strong heartfelt opinions about different brands and types of speakers, but very much like falling in love, when it happens, you’ll know. You may think that you are interested in a large speaker with conventional direct radiating drivers and then one day hear a small electrostatic and discover that it has the sound you’re dreaming of. Nothing you buy will be perfect, but something will give you most of what you want, and the only way to find it is to listen.

Good luck, and enjoy he hunt!...it should be fun.

I formerly worked for a small but respected speaker manufacturer in Australia. (Used speakers made by them are higher than your suggested budget).
Things I'd consider if were I in the market for loudspeakers.

• Cabinet design, the more it sounds hollow and drummy when you rap your knuckles on it, the more energy it will release when your drivers compress air within it in the audible spectrum (bad for accuracy). The cabinet will have it's own resonant frequency. This is where less is more, less uncontrolled noise = more controlled sound. Inert cabinets potentially sound better.
  
• Crossover design. Clever crossover design can produce a good sound, however quality parts in the "recipe" simply confirm that the laws of physics (specifically electronics) cannot be denied.
• Drivers that work well with each other, after all the drivers will be fed specific frequencies from the crossover, the exchange or frequencies where two or more drivers are both providing the same notes (the crossover point) is important. Drivers that match each other in where they perform together within their frequency range is very important.
  
• Synergy of all of these elements and more are something your ears (and personal tastes), will tell you. How they sound in the room, the electronics connected to them, cables..the list goes on.
  

Hello Ty!
 I suggest you start by going to a showroom and listening  to some speakers WITH the brand/approx price range of the AMP you own or intend to buy. Many times amp families have a “house sound”—they have similar sonic characteristics. At the price point you are looking at, most gear will not be neutral, so getting gear that complements each other’s strengths and weaknesses is a good idea. When you find a sound that pleases you, check out what interconnects and speaker wires they are using also. Everything adds to the coloration of your system. 
Those b&w 802 are very nice speakers. You would need plenty of power in your amp to drive them well. The thing about great speakers, they reveal very well the strengths and weaknesses of your system!!! So you may get great speakers, but if you are driving them with so-so gear, you WILL hear that the gear is crappy. Its important to match quality.
 For vintage gear, for good matches, if you like, say the 802s, then read the professional reviews from back in the day. When you see a stellar review, note the amp, the interconnects, the speaker wires they used in their system and then go buy that set up. 
20 years ago, we went to a showroom to listen to gear—with a very well produced CD that had vocals, solo horns, a solo violin, a choir and an orchestra. We tried the same 5 minutes with multiple brands in the $2-4K price range, until we found a pr that did justice to the music the way WE liked it. Then we asked the dealer to recommend a good matching amp. We went home with “last year’s” AMP for less than half price of new and have enjoyed the speakers since, even as we upgraded amps and wires.
We bought Vienna Acoustic Beethoven’s. They were Stereophile B-rated speakers in their day. You can still find them used every so often. They are very musical speakers that do a great job with jazz, small-ensemble classical, and rock. They are small enough to work in a living room. And they are forgiving of mid-fi gear, yet are resolving enough to keep up with much better gear than your budget allows. I’m running them with a vintage amp—Mufi KW 500, ($8k new) and they sound superb. When I bought them, the dealer suggested the flagship Yamaha amp (midfi, solid state and had a built in phono preamp that worked well with 70s era pioneer Turntables).
Happy Hunting!

King Crimson, Ramones & Beethoven.

As luck would have it, those three acts are planning a reunion concert this summer at the Beacon Theatre in Manhattan. Tickets are going fast, so get yours soon. Then you will have the appropriate benchmark for assessing the various components under review.

Tyko,

Our club, AZ AV Club is holding its 1st annual Speakerfest on Saturday 
June 29th 10am-4pm in Scottsdale, AZ. $10 admission fee.
You will hear : Sanders Sound, Joseph Audio, ATC 50s passive,
ZU, Salk, Spatial, Tekton, LSA and Markaudio speakers. Maybe more.
I have no idea where you live, but a RT ticky on SW Air if properly shopped for should not be over $300. Plus our $10 admit fee. You will hear some pretty nice stuff in properly sized rooms powered by D"Agostino etc. Might be worth your while. Some principals will speak
as well. Like warm climates?