Gone though alot of gear myself. Never bought super expensive gear costing multiples of thousands but have spent 2 grand on speakers and a bit more on an amp, both discounted and were closer to double retail.
At this stage, I listen at lower to moderate SPLs whether its movies or music and have two systems, each having an amp, dac and speakers with a source player for discs and the performance I get is good enough to enjoy.
While I could possibly get better, it will require I spend more money with no guarantee I can succeed buying a particular piece that actually is better. I also like the gear I have now.
So, while there are alot of other speakers and some dacs I would like to try, I do not pursue as I will be forever buying and reselling more likely than not. I researched my gear first and made an informed decision, and it seems to work well enough together and are not bulky.
From here, a new direction would be headphones and a streamer...both of which I am not compelled to pursue. I may be near the end swapping gear at this point.