If you want your speakers to match, and I agree it's a good idea to timbre-match, then you'd be better off buying your set all at once. I know you want to piece it together, but the only real reason to do that would be due to budgetary concerns, and it sounds like that is not an issue.
All that said, you are the ideal candidate for a matched Aperion Audio system, in my opinion. The company is great and will let you audition in your living space (free shipping both ways). To be honest, you have a ton of options if you are just looking for speakers in that price range, but unless you want to build that's what I'd try first, personally. You'll be able to get a nice set of towers for music, a great sub, and surrounds to support movie watching.
Alternatively, I've always liked Infinity's mid-range speakers. Their CMMD cones are proprietary, and I've thought they were a great value. I used to be a huge Definitive fan, but they abandoned their old model to expand to larger markets (not that I blame them). I have not listened to the Energy speakers or KEF speakers that have become popular in the past five years or so, but the reviews are positive, and I know you can get Energy towers with a set of speakers in your range. You can try and find some DCM speakers in that range, as well, but it might be tough to find a matched set from a higher-end name at that price.
My advice is to visit a local high-end store, have a listen, go to Best Buy (I mean, why not, right?), and shop around a bit to find what's best for you. See if you can find a B&W, Paradigm, or Tannoy (I love Tannoys) dealer nearby. Take your time and make sure you've found what you want before buying.
Good luck,
Boz
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