Totally overwhelmed (speakers under $5k)

I am newer to the audiophile community and don't have much in the way of higher end gear to be honest.  I have been upgrading things as I go with my home theater (now Anthem receiver, Martin Logan speakers, and SVS sub) and am now wanting to upgrade my music system that is in my home office.  It is currently equipment that was originally in my home theater that has been replaced.  So I have a BasX preamp, 7 channel solid state BasX amp running 2 channel, T2+ speakers, and cabling all from Emotive.  The wires are basic copper speaker wire with banana plugs on the ends.  And I have an RSL Speedwoofer 10"  subwoofer. My source is Amazon Music HD on a Macbook Pro fed to the preamp by an optical cable. All in all it sounds pretty good but I want to take it up a notch.  

The other day I spoke with James at Raven Audio about cables and he said suggested that I would actually get a lot more bang by upgrading my equipment than worrying about my cables (which is fair).  Of course he is a fan of his own brand's amps and speakers but he also said very good things about Dynaudio and Focal (which I do have some experience with for car audio and headphones).  In doing research on the Raven Audio speakers, I have seen people lauding the Tekton Moab, Aperion Verus III, as well as others.  When I do searches for "best speakers under $5000" I get lots of mainstream review sites that talk about brands like Definitive Technologies, Polk, KEF, Klipsch, SVS, and more.  But they generally don't talk about Ravel, Tekton, or any of those. I assume it is because they are too small. 

Honestly though, at this point I am overwhelmed. Too many brands with too many speakers and where I live there are not a lot of shops to go listen to these higher end speakers. I have seen lots of debates on here along with folks that really have their definite opinions.  Here are my requirements and hopefully I can gain some knowledge, insight, and direction from folks on this site that have much greater experience than myself. 

1) I want speakers that are clear and clean with lots of detail.  But I also want to be able to just listen to the music, being immersed without having my ears ringing from the sharpness after a bit.

2) I want to be able to plug them into my current preamp and solid state amp and be able to enjoy them as is.  Later on, if/when I decide to change the amp to a tube amp, I want them to be able to work well with those characteristics too. 

3) I want the new price to be limited to $5k and under.  I am open to used in the right circumstances but hoping to get a smoking deal on some used $15k speakers (like some Legacy's) is just wishful thinking at this point.  With new, you know what you are getting and will have a warranty.  

4) I listen to all sorts of music so it needs to be able to switch between rock, heavy metal, classical, jazz, hip hop, bag pipes, and everything in between.  

5) Subwoofer is optional.  I have the Speedwoofer currently which is know is not perfect for music (ported).  I am fine upgrading to a sealed SVS at some point or getting towers that don't even need a sub. I actually have an older pair of Infinity SM 125's that I got close to 30 years ago that don't really need one.  

6) Aesthetics are a plus but not a requirement.  I am a function over form guy.  Some of these B&W's, Focals, and others look beautiful compared to the Moabs which are more utilitarian but I am not stress about it. 

7) Size can be whatever.  Again, the Moabs appear to be massive and that is fine but so is something that is much smaller.  The room is roughly 14' by 24' with 9' ceilings.  While it isn't an auditorium, it isn't just a small room either.  

Ok, I think that covers it except to say straight up, I don't tend to care for negativity.  If you have heard something and you don't care for it for X, Y, and Z reasons, great, please say so.  But please don't put something down because you don't like their marketing or you believe that it has to be a $100k system to be worthwhile.  Thank you in advance for your responses.