Has technology advanced to the point that digital music can be rendered tolerable, even enjoyable?
Welcome to the forum, and welcome to 2023!
Has technology advanced to the point that solid state amplification can be rendered tolerable, even enjoyable?
You are answering your own questions... Decidedly yes.
The third issue that presents itself involves the old Altec/JBL speakers. NOPE!!! I have not found that they suck. However, given that everything else that I thought I knew was wrong, am I wrong about this too?!?!?
Not if you enjoy them. Speakers and other transducers are yet to catch up with the incredibly high fidelity available from modern electronics, and how a speaker performs has everything to do with the room it is in, so if you've got a fit you like, that's awesome.
The ten million dollar question is, “Where do I go from here?”
You could always get a calibrated mic and do some simple measurements with free software to see how things look, and get an idea of whether you've got anything particularly nasty going on you might want to address.
UMIK-1
The UMIK-1 is an omni-directional USB measurement calibrated microphone providing Plug & Play acoustic measurement. From speaker & room acoustic measurement to recording, this microphone provides low noise and accurate results you can rely on.
www.minidsp.com
REW room acoustics and audio device measurement and analysis software
REW is free software for room acoustic measurement, loudspeaker measurement and audio device measurement and analysis
www.roomeqwizard.com
It really has gotten much easier to get great sound than ever before, and the fact that you are even open to the idea that it might be this easy puts you way ahead of the game.