I must be lucky. I loved my first good speakers, ML SL3 electrostats and they were my mains (with a Velodyne) for 16 years. I loved them the whole time.
I moved into Dynaudio Sapphires and was very happy five years but I'd heard better and got very lucky as I moved into (possible end-game speakers for me) used Raidho D2 small floorstanders. Their sound, room-corrected has thrilled me for six years and I can listen to glorious rich detail with full bass for hours at a time.
I'd be wary of moving in a very different direction to buy an end-game pair. Lots of potential risk is what I suspect. I moved gradually into a speaker type and sound I really love and then got a great pair after fully understanding them.