As a guy who has actually cooked up custom ROM's for one of the early Android phones (Moto Cliq, 1.5 Donut - 2.1 Eclair), flashing custom ROM's, installing custom recoveries, using RSD lite in case of a soft brick, playing around with bootloaders by using cross-hashed zip updates from similar hardware based phones in the same line of phones, typing a story of ADB commands to commit custom ROM flashing and making sure you don't mistype one line of two similar kinds due to possible hard bricking, ROM flashing then was not as easy as the process of doing it today as most things, if not , all are simplified.
There was a 80% chance that you had to learn a whole lot of commands to flash something back then. These day's and thanks to dev's, the process is simplistic, as you said, download an exe, attach phone and make sure development mode settings are on, click exe, let the process begin > continue till end whether be it a root process or custom recovery image etc, is a whole lot different to what user's on 1.5, 1.6, 2.0, 2.1, 2.2 had to do.
While it isn't a technical achievement such as writing a complete program that would compile and execute, but it is sort of a technical achievement at the end of the day. (A good feeling one too, if you don't manage to brick your phone).
I followed early Android ROM flashing and it didn't interest me at all. I've had to write complete programs and don't have any interest in doing the same, for free basically. Is this rocket science? No. Are we using fancy algorithms? Nope.
I didn't write the tools to recover our products from a firmware download failure (a real failure, such as due to power loss during a download), but the source isn't difficult to follow. I don't think any of our firmware developers or my "tools" friends have any side projects going. Either we don't care or are too tired from our day jobs.
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