I'm in agreement that a large portion of your budget should be devoted to speakers. I enjoy the sound of monitors and am a big fan of Green Mountain Audio -- I've owned the Europa and Callisto monitors. Of these, only used Europas would be in your budget.
Other monitors that I've heard and enjoyed:
- Paradigm, Studio series
- JM Labs / Focal, Cobalt series (not chorus)
- Von Schweikert
Monitors I'd like to hear based on feedback:
- Aurum Cantus
Not to complicate the mix too much, but it sounds like you might also enjoy a singledriver speaker. If you've never heard one, and have a chance to do so, you may be rewarded. Most single driver speakers are made by smaller companies or DIY guys.
On the integrated amp front, I loved my YBA Integre. It's a stand out, loved by all owners, and a constant recommended component, if you follow reviews. While this amp is out of your price range, I have heard nothing but praise for the Audio Refinement series by YBA. The Audio Refinement Complete is the one you want to listen to. These can be found used for around $450.
I've owned Jolida equiptment and enjoy its sound -- for a tube option, if you aren't going to use your computer as a digital source (in which case you can buy a tube output DAC to warm your sound), you could opt for a tube output CD player, but you may simply prefer a tube amp.
To that end, you may want to consider the Jolida integrated. The remote is a nice feature, and it is a hybrid with both solid state and tubes giving you warm mids and clear highs with the underside powered by solid state. I used to own the 1501 but have heard the 1701 is an improvement. There's one on Audiogon for $530 obo.
I also hear good things about Eastern Elecric.
If I were to recommend a system for you based on what I've heard you say (rather than pressing my opinion) I'd think about this route:
1. Jolida 1701 Integrated or Audio Refinement Complete: ~$500 (used)
- if you want the convenience of a remote
- if you want a true tube amp with bigger tube sound, then the Jolida 102 (~$400) or 202 (~$500)
2. Speakers should match well with your amplifier. Listen and learn but plan to spend about $700-$800.
3. CDP -- I'll defer to the others on the CDP. My budget pics are the EastSound E5, the Cambridge Audio Azur series, and a few others -- all budget breakers. There is a big difference in sound based on your digital front end, but that's not a discussion worth getting into at your system price point since the money is best spent elsewhere. So ... the Oppo I suppose. $160
4. Cables. Signal Cable Silver Resolution ICs (1 pair) and speaker cables. Upgrade to these later @ about ~$200 (used).