I like a little bit of what you're talking about from time to time, too. I don't view being a ham as having to give that up. If I feel like doing that I flip the CB on and hang out with those guys, or I find the local 2 meter or 80 meter guys that do the same thing. Yes, all of that happens on 2 meters and 80 meters, as well.
There are probably some activities that most leave behind when they go ham, but a lot of them don't. A lot of the freebanders are hams. A lot are not. I gave up freebanding a long time ago, but I did it mainly because it became pointless. There was no need to freeband once I had access to all of the bands where there was more activity, anyway.
Running excess power on CB? Most of the hams that I know that are also CBers (there are a lot here) still run as much power as they want on CB. Why? Because they can and noone cares. It's viewed sort-of in the same light as going 75 mph on the 65mph speed limit freeway. All of the traffic is moving at 75mph and nobody is handing out tickets for it. I guess what I'm getting at here is that if you're a ham, you know what the rules are, but it's still up to each individual to decide for themselves what they want to do.
For me, I enjoy experimenting and learning about new things that I haven't tried yet, especially just to see if I can do it. My recent playing around with hitting satellites with a handheld radio is a good example of this. I would hazard a guess that most people on this forum are the type that make a hobby out of radio - they aren't just here to learn how to hook up a radio in their car and move on. The part of ham radio that is appealing to me is how there just doesn't seem to be any limit on "what to try next", no matter what your budget is.
I do think the location of the testing is a barrier for a lot of people. I don't have a good solution for that, but it seems like there should be a way to remove that barrier.