The frame element has been completely removed, the hgroup element is gone, and so is the dir element. acronym is deprecated in favour of abbr. isindex, plaintext, xmp, and listing are all dead.
The attributes border, clear, background and bgcolor have all been removed by HTML, and shifted to be CSS' responsibility instead.
Just moving between EPUB 2 and EPUB 3, you lose the DAISY format support, and external resources. (EPUB2 let you use full URLs to specify parts hosted externally, like webpages, but EPUB3 requires itself to be self-contained. Not a bad change, but still a breaking change.) NCX replaces just using a HTML5 nav element, and a few more things.
All of those things mean that there _are_ technical documents that exist, that _aren't_ readable without some effort to update them.