Particularly with digital sources, unless you are going out of your way to use a crappy source, differences are marginal. Accurately Converting a digital signal is a very easy and cheap thing to do with modern technology, isn’t much room for improvement by spending more. The THD of the DAC circuit in a $10 USB to 3.5mm adaptor is 0.01%. Which is about 1/10 the amount of distortion that would be audible even with the best ears listening to be best system.
The Signal to noise ratio of the Apple dongle is 99 dB, which means you would need to crank the volume to 99 dB to get 1 dB of unintended noise. For reference the ambient noise in a fairly quiet room is 20-30 dB and 85 DB is when you start damaging your ears, so you would have to turn the volume up to injurious levels to create 1/20 the amount of noise in a quit room. If you want spend thousands of dollars to make the noise and distortion even more inaudible than what you already couldn’t hear, of course someone will be happy to sell it to you.
With speakers, because you have mechanical motion, there will always be things flexing and rubbing and vibrating, so there is far more room for improvement. Analog, by definition requires mechanical movement, so again there is more difference between the signals produced by different analog devices.
You can always rationalize a reason why the new one is different enough to make it nessidsary… I have closed back and open back headphones, but those are both dynamic drivers, so of course I need a planar… So you get some Sundaras, but maybe now I need a closed planar…