I'm interested in building my own radios for use on the air. I'm still rather new to electronics so I'm looking for simpler projects that I can build to learn on the way, and I'm thinking that a CW transmitter and/or receiver would be appropriate (unless someone wants to tell me otherwise?). I've been reading the ARRL Handbook and "Experimental Methods in RF Design" trying to find the information needed to build one of my own but to no avail. While there are circuit diagrams available in those texts, even the simplest ones are too much for me to understand (I did read the accompanying text) and I feel like if I were to just build it and have it work, it wouldn't progress my understanding of it at all and I'm not confident in my ability to build something large without error if I don't have the possibility of testing the smaller subcircuits individually.
Looking at the block diagram below, I decided to look into the workings of an oscillator, since it doesn't need any other parts of the radio to function, so it'll be easier to test on its own. I understand how a simple RLC circuit behaves (mathematically), but when it's combined with other components to make a complete oscillator, that's when I get lost.
"Experimental Methods in RF Design" mentions the NE602 IC which has an oscillator and a mixer, making it easier to make a complete radio. Another way I could go is using this for the radio and work on the amplifier and antenna, then replacing the IC with discrete components, but I couldn't find any circuits using this IC that are simple enough that I can confidently build it error-free.
Any advice on the path I should take (be it one I've mentioned above or not) and useful resources to get me started or get past the barriers I'm facing?