Advice on making a speaker change

What an exciting opportunity!  I too am a “buy and hold” investor when it comes to all things audio, but at 38 years, you’ve got me beat.  (I’ve had customized AN-Es for almost 15 years now.)  One thing to keep in mind is that your hearing - both physically but also your taste and values - has likely changed in that time.  

I have a very good friend who loves the Wilson sound.  We listen to and really enjoy each others’ systems - his a high power SS and digital system built around Wilsons, mine a low-powered tube snd vinyl system built around the Audio Notes - but we wouldn’t trade ours for the other’s.  Why?  We listen differently and value different things.  He prioritizes imaging and frequency extremes.  I’m a tonality/midrange guy.  The cool thing is we’ve come to understand better our own values through our engagement with each other’s systems.  

My advice - which I’m following myself as I contemplate one day replacing my own beloved speakers - is to listen to as many different types of speakers (and systems) as you can.  While you’re surely right that it’s hard at shows to isolate exactly what you want to listen to, I’ve still found it incredibly helpful to identify themes in my preferences.  

I’ve attended the Capital Audio Fest the last 3 years, and there are very few systems (above a certain $ threshold) that I can’t find enjoyable in some way or another.  But what I’ve discovered is that for me, less is more.  I’ve been blown away by the immediacy and realism of a number of systems that seem to reflect a “do no harm” aesthetic, manufacturers that have no or minimal crossovers, like Rethm, Songer, Fern & Roby, Voxativ and Cinnamon, or other highly efficient, horn based speakers by the likes of Cessaro or Triangle Art.  I can still admire the Borresens, the YGs, Estelons, Rockports, Vandersteens and the like, but I’m a low power tube guy at heart, so that helps narrow the field considerably for me. 

Whatever you do, good luck and enjoy the journey.

@mdalton Like you, I have been going to shows and trying to make a short list of choices for a while now, in anticipation of making a change some day. If I didn't still think the KEF's sounded really good, or they would just "blow up", it would be much easier to "pull the trigger". They can be like an old friend. Shows are great for exposure but can be frustrating for critical listening. I'll be taking some road trips to dealers for further auditioning, but different electronics and rooms can make that a challenge too. Thanks again for the thoughts and input. 

I would say jump!  But it's hard to say jump into which pool since you didn't share any budget.