The Amatur Radio Relay Leage (ARRL) has a page with overview on ham radio and information on how to get licensed[0]. The wikipedia page also provides a nice overview[1]. The ARRL sells books which can help you learn the material for the license exams. You might also see if there's an amateur radio club near you; in my experience they're pretty friendly and interested in helping out aspiring hams.
"in my experience they're pretty friendly and interested in helping out aspiring hams."
Talk to people who have been there about station building experiences. I think the answer you'll get is the best maximization of fun is spending around $1 on antenna system for about every $1 spent on radio gear. Hooking up a $1000 radio to a $50 antenna system is likely to be far less enjoyable and lower performance than hooking up a $50 radio to a $1000 antenna system although its about the same outlay of dough and effort.
Also the old timers are pretty good at planning, having been there, and the best antenna system for a plot of land is not necessarily the most expensive or largest.
The main problem you'll find is technological changes, at the feedpoint auto-tuners hit in a big way maybe 20 years ago so maybe 19 years ago you wouldn't get good advice about them or randomwire antennas in general. (OK now, probably). Maybe 30 years ago it took awhile for hams at that time to "grok" ferrite based baluns. I'm not sure what todays misunderstood hotness would be, probably remotely controlled/tuned antennas like magloops with russian vacuum variable caps or those (expensive) steppir things.
Also its a very big hobby. Someone who thinks they've experienced it all either is extremely old and wealthy or is wrong.
It turns out that on the extreme end, the ratio grows to $4 or more per antenna for $1 in radio/computers/etc. A well-equipped tower can have $10,000 worth of parts. This does not count the labor.
The scale range of fun in Ham Radio is quite large.
True, but don't forget SO2R and multi radio contesters, and there do exist $10K tower systems but there also exists radios like the $10K IC-7800 or the merely $8K IC-7700 series. So it is possible to maintain the 1:1 ratio.
Its not entirely audiophile. Impressive engineering, cutting edge stuff, for that price. IP3 of +40 dBm? 110 dB dynamic range IF strip with multiple AGC loops? how the...
The ARRL Operating Manual is excellent. It's appropriate for a complete newcomer to just pick up and start reading, but will go into more advanced topics, like antenna design and satellites.
If you're not licensed, there are flashcard apps for your phone that will prepare to completely ace the test very quickly. The manual's a good reference for any questions you don't understand. I'd also recommend finding a local club or other operator just to get a demo of a basic radio contact and the protocol people follow for conversation. Some of it's mandated by governments, but a lot of it just convention.
[0] http://www.arrl.org/licensing-education-training
[1] https://en.wikipedia.org/wiki/Amateur_radio