Kinda want one. Any you guys mess around with a ham radio?

used to , let my license go about 2 years ago

CB won't work for you Huh?
How far do you want to talk?
just

My buddy and I have thought about it, but I don't know much about it.

We would want to talk the equivalent of neighboring states apart for distance. Is it expensive to get into or complicated? Is it something for SHTF or I guess if towers are out that means no signal for communication.

the license isn't expensive , you can get a decent radio for your truck for around 300 with an antenna

first step is go read the book take the test , get the license , you will learn enough about it in that procces that you will have a better understanding of what it can and can't do

I have a couple of these baofeng AR5RMs. Current just using them on FRS frequencies, which are the same frequencies as cheap 2-way radios. I also have a couple cheap two way radios, so I can hand them out to the kids when we're out hiking or whatever, so we can keep in touch. They work pretty well, and they can also do ham frequencies. The ham radio club up in Lincoln has classes for the technician license at the end of this month that I'd like to attend, if the guy running the class ever emails me back.

Could a truck mounted radio stretch a few hundred miles as the crow flies?

You will most likely not have reliable communication a few hundred miles, even with a repeater. With a repeater on 2 meter or 1.25 m you will likely only reach our 50 - 100 miles (unless you have some unusual atmospheric conditions causing tropospheric ducting). To reach distances of a few hundred miles you will need to be using High Frequency (HF) bands and most likely using more power than a standard truck radio. Also Technician licenses are very limited on HF and only using Morse code. If you want to talk that far, look at HF and upgrading to a General or Extra class license.

I got my technician license this year but have yet to get a radio set up yet. Got a couple of those handheld baofeng that work pretty well but are limited wattage.

if you both park on top of mountains with line of sight

but repeaters can do a lot , from SE Green county I could hit Delafield and Baraboo repeaters , use Brodhead as your nearest city to run a milage on that.
there are also voip repeaters you can hit to go across the internet

Been a ham for 31 years now. What are you looking to use it for? For close range comms check out GMRS.