My two cents:
Radio is radio, be it GMRS, CB, FRS, Ham.
The only difference is the frequency used and the license requirement.
For someone that applies themselves, playing cb radio can in fact be a learning experience.
The more you apply yourself, the more you can learn, the more you will be able to do.
The radio and the power factor is just a small part of what it is all about.
In the 60's and early 70's - when the legal operators played by the rules, the antenna manufacturers went out of their way to make antennas that improved a meager 3 watt AM signal to something perceived as being more.
In the 60's / 70's - automobiles used lot's of metal in their body and made a perfect ground plane - the metal counterpoise beneath the antenna.
The metallic body gave the installer multiple options - where it could be installed.
The lack of other rf equipment inside of the vehicle made it possible for the user to have a fairly decent signal. The only hindrance was the spark-plugs and wires made ignition noise.
Knowing that a real cb radio antenna needs to be about 9 feet long, the body panels needs to be bonded together, and the antenna needs a counterpoise beneath the antenna - all these things will improve your signal.
Just increasing your transmit power does very little to improve your reception.
Transequitorial propagation - skip - in the winter, allows people in the southern half of the USA to receive those Spanish speaking stations, and to work them, even with just a couple of watts - if you have a good base station antenna.
As with all buddy groups, if you want people to talk to, you need to develop your own buddy groups.
I think the biggest problem today is the lack of free time.
There is always more things to do then there is hours in the day.
TV, cell phones, the internet, sports, family, having to work multiple jobs - just to stay afloat, has killed radio. We just don't have people monitoring the frequencies anymore.
The ones that does, doesn't always come back to a stranger - because it it cliquish.
Too many times a person will try to get into radio, just to find out that there isn't many people locally monitoring the frequencies. Even CB - with 40+ channels, it is hard to have someone on more than a couple of channels, and even then only occasionally having their radio turned on.
Buying just one radio really won't help your cause, you need multiple radios and family and friends willing to use them. That rule, in the early days of CB radio was what made it popular.
In those days, it was like being able to monitor cell phone frequencies.
You could hear some interesting conversations, which gave it a voyeuristic attraction.
Since the world has moved on, those people are no longer there to monitor the frequencies, or talk to.
Throwing good money after bad on something that probably won't get you much satisfaction is a money pit.
Maybe you would be better off just taking the plunge and getting your amateur radio license ticket.