Jean-Louis Gassée's Monday Notes about tech and Apple. He's been in the business since the 60's, worked at Apple in the 80's, founded BeOS: https://mondaynote.com/

Raymond Chen's The Old New Thing. He's an engineer at Microsoft that has been blogging about maintaining legacy systems, Windows and MS-DOS for over 2 decades. https://devblogs.microsoft.com/oldnewthing/

Hackaday is a good blog too, there's many authors so it can be hit or miss but it's full of curious folks. https://hackaday.com/