Agreed re: some of the Windows "strangeness". I think there was some amount of needlessly "Enterprise" architecting going on at MSFT back in the day.
There were also very practical solutions incorporated to accommodate the constraints of the hardware of the time that come off looking like needless complexity today, too. (There's also, arguably, some laziness in the old binary file formats that were nothing more than dumps of in-memory structures. That's a common story across a ton of old software-- not just MSFT.)
Rob Mensching, who worked at Microsoft on Windows Installer pre-release, has a nice blog post about internals of MSI.[0] He goes into some of the overwrought architecture in MSI, as well as quirks to overcome performance limitations in a world of floppy disk-based distribution and much smaller memory capacities. It's a good read.
There were also very practical solutions incorporated to accommodate the constraints of the hardware of the time that come off looking like needless complexity today, too. (There's also, arguably, some laziness in the old binary file formats that were nothing more than dumps of in-memory structures. That's a common story across a ton of old software-- not just MSFT.)
Rob Mensching, who worked at Microsoft on Windows Installer pre-release, has a nice blog post about internals of MSI.[0] He goes into some of the overwrought architecture in MSI, as well as quirks to overcome performance limitations in a world of floppy disk-based distribution and much smaller memory capacities. It's a good read.
[0] https://robmensching.com/blog/posts/2003/11/25/inside-the-ms...