I've traditionally used a combination of sources to learn about various things. Typically a textbook or two and technical manuals for products. Some examples of the latter being lots of old Heathkit manuals, the Tek 321 and 465 manuals, US army PRC-77 manual etc. These are fundamentally very well written and easy to read and you learn a lot from them.
Can anyone recommend any more, particularly covering superhet design, SSB and antenna systems?