@phasemonger & @cdamiller5
Very happy to read your posts, as I was thinking about this yesterday.
Anyone who is (or was) a musician, and there are many in the Audiogon community including myself, is aware of listening as a skill. It’s taught in a musician’s first month of training, and refined over subsequent years.
Listening skills required to play in an ensemble or band readily transfer to listening skills helpful for evaluating an audio system.
The OP has this advantage, as he was also a student musician. French horn, as I recall.
Listening skills required in other professions also apply. Heavy mechanic comes to mind. Physician. Pilot. Therapist.
So, as far as the Audiogon community is concerned, the answer to when, is often now.