I had a similar mental exercise, trying to compile a smaller system I could use in a den with a sound characteristic I could live with. It would have to be tube-powered, and speakers small enough to give a good reproduction range yet have deep bass and a sound that isn't too forward or bright. And then, I get tripped up along the way when trying to choose a digital source I can live with.
While I can't recommend sources (some prefer digital server/streaming, some prefer CD/SACD, some prefer analog), and certainly can't recommend speakers (again, it's way too subjective for me to suggest anything), I would base it around a Conrad-Johnson CAV50 if I could find the right deal on one. (The newer CAV45 is more money.) Sadly this is the only component I could decide upon. And it would take some hunting to find one for around $1,250. There is also the PrimaLuna Prologue 1 (integrated amp) that can be had for around the same price or even less. Another good choice IMHO.
So unfortunately, I guess I'll have to bow out on most of this $2,000 challenge. I have the anchor picked out (the C-J or the PrimaLuna), but the rest I really have no options to choose from until I get out to hear more components.