Ah, glad to see the mods moved the thread....
So, as with most issues regarding equipment, the million $$ question is: Who are you going to be talking to? If you just go 'wheeling with your buddies and you only need to be able to communicate with them, that hand held CB may work just fine (as might one of those handheld FRS/GMRS radios that are sold everywhere in blister packs of 2.)
The biggest limitations of the handheld are the low power (which will limit your Transmitting range) and the small antenna, which will limit your transmit and receive (TX and RX) range.
A mobile will get you more power (up to 4 watts PEP, IIRC) and a large, high-mounted antenna will make it easier to communicate.
Of course, with a HAM you can, in theory, get up to 1500 watts PEP, though I can't imagine anybody putting that much power out of a mobile unit. However 50 watts - which is to say, more than 10x what you can get with CB - is pretty standard in most mobile 2m rigs. 2m and 440 are also FM, which means a clearer signal, and the ability to hit repeaters - which are all over the country - can give you significant range.
If I was to say there's one drawback to HAM, it's the level of commitment it requires. Getting the license is easy, but getting into the hobby is something that will require you to try to absorb a lot of knowledge that you may not care to. Just reading the owners manual for my 2m radio was like reading sanskrit to me and I've had some exposure to it before.
It's not that it can't be done, it can. It's just that, the way I see it, time is a zero-sum game: Every hour I spend trying to figure out how to use my radio is an hour I can't spend doing something that I consider more valuable. It's unfortunate but HAM gear is aimed towards the 'enthusiast' who has the time and desire to learn all this stuff (no surprise, as that's where the money is.)
The downside of this is that people like me who just want a reliable radio they can use on the trail are often put off by the complexity and the steep learning curve required to really get much use out of the equipment. For that reason, we fall back to the plug-and-play CB which requires no special knowledge or even a license to operate.