alt Hacker Newsgeerlingguy and simonw really amaze me at how well and consistently they cover their respective spaces of interest. Great content, easy to read, and thorough! I'm sure there are others doing deep reporting like this on their own subjects. I'd love to read them too.
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/