A timely blog post for me: A close friend who is the same age as me (and an EE) has been trying to get me into Ham for over 10 years. I finally became interested and bought a $25 radio (BaoFeng UV-5R) on Amazon ... only to learn that I couldn't talk to my friend on Day 0 because 1. he lives >20 mi away, 2. no line of sight and had to learn about repeaters, and 3. I have to learn technical and cultural nuance of Ham before being allowed to speak. The proposition value that Ham is not an "old IM client" and instead a toy for analog protocol nerds took a long time to understand.
Edit: added radio model, fixed price