You've gotten some great responses!
I'll add a little more "food for thought":
On value and diminishing returns:
As stated this is very unique to your own experience.
Factors are:
1) What is a dollar worth (to you) - if you are pulling well into 6 digits salary, your solution is likely more than if you are in the mid 5 digits. Their is a lot more to it than that, but willingness to part with your earnings is certainly a big influence!
2) What is your reference for sound quality - Are you around live music much? I'll never forget my trip to get my Phil3's from Dennis Murphy. I brought a pair of Focal Solo6 speakers for him to listen to when I was there because I thought they were pretty special. We hooked them up and Dennis cued up a full-on orchestral chord and in about 45 seconds, he was done (wtf)! He told me they have a very similar sound character to the RAAL ribbon tweeter (generally considered a "world class" tweeter)! Aside from his time designing speakers, occasionally tweaking a speaker from a major manufacturer (to "fix" it) and measuring 100's of speakers, Dennis plays Viola (and violin) in his local orchestra! He knows what that full-on orchestral chord should sound like and his experience measuring/designing/tuning speakers means he has been critically evaluating
speakers for decades! So I have to believe he is way better at this than the average dude!
3) How good is your hearing and mental process involved in sound perception? Obviously some people have better hearing (genetic, damage from exposure to loud noises, etc). At some level it is reasonable to believe some people simply have a higher level of resolution than others. A good analogy might be how for some people the "magic eye" 3D pictures immediately pop out at them and others struggle to make out the hidden image (and I have no idea which indicates better perception - on the one hand, being able to quickly see the image seems superior, but on the other, most dogs will not recognize their owner's voice on the phone speaker - even calling their name - presumably because their is so much missing from what they hear live)! As another visual analogy, I have "the curse of the level eye" - if I walk into a house and the top of a door is not level, or the corner where two "right angle" walls meet is not 90 degrees, it pops out at me. I have no control over it, and would not easily live in a home where the lines are not reasonably level/square. So I'd assume there are people who are extra sensitive to certain inadequacies of sound from speakers in an analogous way.
4) How picky are you? I started critically listening to speakers when I was roughly where you are - ready to upgrade to the great sound system I always wanted. I listened and compared many speakers in direct A-B comparison in my home with generally at least 2 days of listening. Going through that process, I ended up picking out some pretty good speakers. $3,000/pr is the most expensive I have bought. The interesting thing is that I am really not that picky - I find I can really enjoy music on pretty inexpensive (but not poor) speakers! An example is the Infinity R162 bookshelf speakers (along with a subwoofer, but we'll leave that for later) which run $180 to $200 when they are discounted (which happens a few times a year). Below is a thread where I discuss them. I intellectually know I have better sounding speakers, but good music is good music, and I am very happy to listen to it on these speakers. I wonder if, by making such a quest out of getting the best speakers I could I didn't "over-buy".
https://forums.audioholics.com/forums/threads/infinity-speakers-back-on-sale.114900/#post-1318896
Where to start:
If you have a Best Buy Magnolia room nearby, try to listen to some Martin Logan
electrostatic speakers (doesn't matter that much which as they generally have the same character)!
See if you can find some Klipsch LaScala or, at least, Forte speakers (current model - they have been refined over the years).
I love both of these speakers, but they do not sound at all the same! The Klipsch have dynamics out the yen-yang and the electrostatics form an amazing soundfield if you are in the exactly right sweetspot!
And here you are starting to see the conundrum - I cannot recommend the best speaker for you! Hell, I can't recommend the best speaker for me! Now if you tell me what song I will listen to, then I will generally have a preference for which speaker sounds better! If I could only have one, something in the middle ground such as the Philharmonic BMR or Focal Solo6 is a good option!
The bottom line is getting perfect sound out of speakers is a very difficult task and invariably, the designer/engineer has to pick and choose which compromises he is going to make! Similarly, you have to pick which trade offs you want to listen to.
So if you can find the ML electrostats and one of these Klipsch speakers and report back your observations, it would be useful for us to be able to help you narrow down the sound you are looking for. Their are plenty of others, but these two represent what I consider extremes and are useful for sorting out your specific preferences.
Some quick comments on how to listen:
1) Bring music you are very familiar with and try to have a wide range of sounds/styles. The dynamics of the Klipsch are going to favor them for music that has lots of energy, and the Martin Logan can make it sound like a singer singing a delicate/soft passage is singing in your ear with incredible intimacy!
2) Try to start each song with a fresh, open mind - if, initially, you notice one speaker does a particular thing (good or bad),you have to be careful not to repeatedly home in on that one aspect to define the speaker while missing others.
3) Be sure to check with the sales guy that you are listening without subs and in "direct" or "pure direct" mode - no room equalization (or loudness/tone controls) in effect!
4) If you are switching back and forth between two different speakers the louder one will have an unfair advantage. Hopefully there is a way to level-match them.
We can guide you to good speakers, but you have to choose the ones that are right to your ear! If you provide feedback on the ones you try out, where we are familiar with that speaker, we can help you on what else to try.
In the up to $1000/pr category, I think Harman Audio rules the roost whenever their Infinity Reference or JBL Studio Series 5 are on sale. As you get into a higher level, ID companies start to make a strong showing (but still keep an eye out for traditional brands
being closed out).
One thing to consider is going back to item 2 above- "What is your reference for sound quality". Lets take an extreme example. If all you know is TV speakers, anything will sound good and it is easy to get enamored to a pair of speakers that you might later realize have significant deficiencies which did not stand out since TV speakers present such a low bar! I know you are familiar with sound from headphones so this is probably not a concern, but I never consider it a bad idea to get a pair of well recommended bookshelf speakers (because of lower price than towers) that pass your initial audition to use as a stepping stone to refine your ears (and see how happy you would be to live with them). I am struggling a little with how good of a reference headphones are because it is a much different presentation when the sound is at your ear and the sound images in the middle of your head (and I don't listen on phones that often).
Generally, a competent speaker manufacturer will have the same sound across their different offering in the same model series. Consequently, it is easier to audition at home (assuming you have local dealers that will allow you a grace period for returns) using the bookshelf models, but do pay attention to how similar they sound in the showroom.
For example, if you are interested in the SVS Ultra series, it is much easier to order/recieve/setup the bookshelf speakers than towers. If you like them, then you can order the towers with the intent of using the BS speakers for surrounds or just return them.
Also I am a fan of the value of bookshelf speakers (depending on your budget). For example, you can get (I am assuming prices have not changed) the SVS Ultra BS speakers for $1000/pr or the SVS Prime Towers for the same $1000/pr. For me, this is a no-brainer - you want the extra refinement of the Ultra series. You would want a subwoofer with either of these speakers, so the added bass of the Prime towers is not really a benefit. I have always liked a good pair of bookshelf speakers with a good subwoofer and you can see that RSL is committed to this model (no towers).
Also, here is a very good write-up TheWarrior did on listening to various speakers at differing levels of performance that you might find useful:
https://forums.audioholics.com/forums/threads/bookshelf-speaker-shootout.95335/#post-1089348
Good luck and
enjoy the process!