Here's my reasoning, to be acted on in the next month or two
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I'll be using mostly the 2M band, and mostly to communicate over longer distances with greated fidelity than cb and frs offer, but mostly those distances will be simplex among vehicles in the same group...mostly.
So, I'll be getting the HT first...five watts is plenty to go the distance between vehicles most places on the same trip--half a watt was plenty the other day going between one side of Keystone and the other on GMRS frequencies. The HT means I can spot other vehicles (tho I'll be getting spotted via hand or GMRS radios til I have a mobile as well) clearly and effectively.
I can also take the HT in the backcountry where I don't have the vehicle--hiking, backpacking, backcountry skiing and snowboarding, MTB, or anything I see fit.
Yaesu makes a couple weatherproof HTs, the VX-6R (2m/6m), VX-7R (2m/6m/70cm) and VX-170/177 (2m/6m only, respectively).
I'll get the mobile when I have the time and money to invest properly in the setup like some of the other guys here.
-Sean
*edit* Uh...like k6uk says below, I was remembering things wrong...substitute 70cm for 6m most places up there and it's mostly correct...