noromance,
"Save for longer and make substantial upgrades less frequently."
That's been my strategy too. Back in the day it was like start with a Dual turntable, then upgrade to a Rega 3, and finish with a Linn LP12.
With amps, the NAD 3020 was the entry point, or sometimes the Nytech/ Arcam A60, and then it was suggested to move up to a Naim amp and climb that ladder.
Even back then the idea of a Naim active six pack seemed fairly ridiculous.
Six boxes just for amplification?
To make things worse a few reviewers suggested that simple integrated amps from the same manufacturer could give better, more coherent sound. Hence the popularity of the basic Naim 42/110.
The only relative ambiguity back then was regarding speakers. The suggested Linn ladder of the Kans, Saras and finally the Isobariks (active) had a few dissenting voices even back then.
There were alternates (Heybrooks, Celestions, Monitor Audio, Mordaunt Short, Naim SBL etc) but there was no obviously defined hierarchy.
The sheer choice over loudspeakers has only increased with time. It must be quite bewildering for newcomers today faced with so many different designs.
I tried to stick to only substantial upgrades but inevitably there were still a few timewasting sideways steps. Maybe even a few backwards ones with various cartridges.
The system item that changed the most was easily the loudspeakers, with the pattern generally being an increase in size. I wish it weren't so, but in my experience bigger has been better.
One reason is the sheer sense of ease coming from the large drivers. It's not a huge difference, but it's there. This was the system change that made the biggest difference in sound - by far. No two speakers sounded the same.
In those pre internet days, I bought everything new. Although it's far easier to experiment with upgrades nowadays, I'd still suggest aiming only for substantial upgrades.
It could be likened to mountain climbing without the danger. Its difficult and expensive and mistakes can be costly. You will find not only many different routes to the summit, but also many different summits!