I guess I was really lucky that I started out on a bbc micro, then got my hands on a c64, then an Amiga, before finally beholding windows 3.0.
By the time I landed in the DOS world aged 8 or so, qbasic was my playground, and was easy to understand from the get-go, and Borland was where I cut my teeth writing something other than basic. One thing it took me a while to get my head around was that a 286 was not a 6502, and practically every little hack, address, anything CPU or memory architecture dependent thing I had learned was now irrelevant.
Coming from Amiga workbench to windows actually felt like a downgrade in many ways, but it was the computer available to me at the time, and retrospectively a good move, as by 3.11 it was clear the wind was blowing to PCs.
Either way, for me, growing with the machine was absolutely formative - the abstraction grew as I did, and I had started near the bottom.