the big one: how do you choose speakers? By what features, data?

Just from personal experience, in the price range you’re looking at, the KLH Model 5s are a great speaker for the money, and used would easily be affordable.  I replaced mine with Harbeths, though I have no intention of letting the Model 5s go, and honestly, they really held their own against the SHL5+ XDs.  The Harbeths sound better, but the KLHs certainly don’t have anything to apologize for.  That said, the Harbeth P3ESR XD also seem like a really good option, though I don’t have any personal experience with them.  I was considering the MoFi Sourcepoints before I bought the KLHs, and would still like to hear them, though I doubt the Harbeths would have to worry about being displaced.  Good luck with whatever you decide on!

@jeffseight it was not my intention to hold back my location. Apologies if I gave that impression. San Diego, CA

@kennyc the 8 is on my radar. I have a small-ish room, it would be perfect.

@jdougs I love the KHLs. I am a die-hard collector of any Henry Kloss product.

Years ago when I auditioned the KEF LS50 I also demoed their R700 which to me sounded similar to the LS50 but with more extension. Perhaps a used R700, R900 or the newer models R7 and R9.  Maybe buy a used LS50 to see if that’s the direction you’d like to go then sell it to buy a floorstander?

@kennyc I don't know what I want, I do know what I don't, based on what I have heard.

No KEF, B&W or Klipsch (never heard the Heritage series, so I mean the other Klipsch) and then a bunch of other brands that start at 3K.

I also prefer a bookshelf speaker, from where I sit. To me the KLH 5 is more of a bookshelf.

Maybe LSA speakers:

https://www.underwoodhifi.com/products/lsa-speakers