You can do a lot with $2K if you research and shop used. Example: I bought a pristine pair of Dahlquist DQM'9 speakers for $270 ($1299 when new). They are in perfect condition front to back and sound wonderful. They're 95db/watt efficient and don't go below 6 ohms so they are an easy load to drive (my 3 watt 2A3 amp does very well). I bought an Adcom GCD750 player (their best) for $600 ($1,400) new. Allow a couple hundred for cables and you still have over a grand for an amp. Don't underestimate the importance of amplification.
Unfortunately there is no simple answer. The number of speakers out there is mind boggling. I really like Moth Cicada's at $699. Upscale Audio has some PSB Image 7PT on special for $849. This is an amazing deal (like half price for NEW speakers)and another speaker that is easy on amps. Built in powered sub and the speaker Tuberoller listens to. Really, if I had the space I'd be getting a pair.
If your serious about this, are you planning on a seperate headphone system and speaker system? This is a pain IMO. You can sell off your HP gear, except the cans, and combine systems and spend a little more. I would recommend a good integrated amp to save on both components and IC's since you don't have an unlimited budget. Plus it's a cleaner solution which is important to me. There are amps that do well for both. I've been listening to a Moth prototype that's a 20 watt tube hybrid that sounds great with headphones and speakers. If it's built it will cost around $600. If I started over now I'd probably do this amp with the PSB's and a $500 CDP. Done for $2K-headphone amp, speaker amp, CDP, speakers!
A little story: My first experience with the Dahlquist speakers was 20 years ago. I was into rock and metal and wanted a new stereo. I had a good job and had some money to spend so I went and auditioned some gear. The DQM-9's sounded real good so I bought them. Since I wanted them loud I bought a 300 wpc Hafler amp (to drive 95db speakers, ouch!). I didn't know much about Hi-Fi and neither did the kid at the Hi-Fi store. I had a few bucks left over and needed something called a preamp so I just got a cheap one since, hell they just select the source and adjust volume. Those speakers only needed 20 or so watts to max out and they cried uncle more than once under the power of that Hafler. Fast forward 15 years and I stepped into a high end store looking for a system. They recommended one which would have me spending considerably more on amp and source than speakers. I walked out thinking they were crazy. Lots of money and a few years later (and much wiser) and I'm listening to the same Dahlquist speakers with a 3 watt tube amp costing twice what the speakers list for new and they never sounded better. I've heard $10K B&W Nautilus speakers demo'd with a $500 Rotel integrated amp (no kidding) and they sounded like crap. I've also heard the other end with $2K Totem's paired with $10K worth of amps and sounded wonderful. Moral of the story: System matching is CRITICAL. It almost doesn't matter what you spend, you can get great sound in almost any price range if your careful and make well informed decisions.
Thanks for reading my rambling