I just wanted to throw something out there regarding handheld radios. Let me preface by saying that not only did I stay at a Holiday Inn Express once, I'm also a licensed HAM radio operator.
5 watts, the max most handhelds can transmit at, isn't a ton. Think of it like this. If each of our trucks is 1/4 mile apart and we have 15 trucks, the distance between Lead and Chase could be 3.5 miles. Over the river and through the woods at 5 watts with an antenna inside the metal cab could be pushing it.
If we do have trucks with handheld radios in my group, we'll stick them near people who can relay with Mobile rigs should it be an issue for Chase or Lead to hear them clearly. That, or we'll move them back or closer up front.
Funny story though, I reached an IRLP Repeater in Portland while sitting in my tent on Mt. Hood while transmitting at 2 watts. That's about 70 miles away! Granted I was sitting at 9000 feet, but it illustrates how a clear line of sight and some altitude can really help.
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That said, an external antenna will help a ton. I believe Big Blue used my handheld with the external and it worked pretty well last year.