Yo, Dave here. No comments specifically on particular cell phone amps. Heck, I just /got/ a cell phone this year!
I would think that an external antenna would be an excellent addition for the somewhat non-intrepid traveler, though. This alone will probably do wonders for the range of your phone. What little I know about the cell system would barely pass for complete ignorance. I believe that the max a cell phone can radiate is 3W, which is around 10X what most handheld phone internal transmitters can do. This is a 10dB increase in power and would work out to around double the range in the city and probably about 4X range in open terrain line-of-sight. It ideally takes about 6dB increase in power to increase range by two. An easy to remember rule of thumb is roughly 10 times, or 10dB, power increase to effectively double the range with some assurance, 6dB is technically 4 times increase in power and assuming ideal conditions you'll double the range. Mostly though to get double the range you need more than 4 times the power, which allows for marginal conditions.
An external antenna is going to do about the same, heck even a unity gain antenna mounted outside the car is going to make a HUGE difference in efficiency, since your truck acts like a very good Farraday cage for 800MHz frequencies. I'd say that the combo of an external antenna and a 3W amp would do around 20dB increase in effective radiated power (basically 100x times the external ERP of just the phone inside your car), which is going to give you around 8x to 10X the range when working line of sight. Which, is BTW, an important point. Cell phones (and really anything at and above 2M wavelength) is line of sight. All the power in the world isn't going to help if the receiver/transmitter (i.e. cell tower) is beyond your line of sight. On level ground, that means about 10 miles max, so keep in mind that going to higher ground is key.
Anyway, to answer your questions, yes on both probably. I would definitely add an external antenna if you need cell coverage. That will help a ton. Add the amp if you find you're still marginal. But it all depends on a cell tower being reasonably close, by which I mean like 20 or so miles. An antenna and amp aren't going to give you cell coverage in the middle of the Yukon or something, though.