Many have given their opinion on this, some with actual experience.  Listen to
them.  I'm not currently doing what you are wanting to do, but did for many
years.

Don't go with a handheld.  They don't have enough power.  Opt for a full power
single or dual band VHF/UHF FM radio.  Even then, you'll have times when the
terrain will separate you enough that it won't work.  I used to run a 30W 2m
mobile with good antenna, and would frequently lose the tail end of the group in
rolling hills.  Having a repeater is fine, if there are any around, but this is
going to depend on where in the country you are riding.  The same goes for
paying attention to what's going on around you.  In a group, you already know
you have to pay attention that someone doesn't do something stupid, but when
spread out it isn't much of a problem and all you have to do is worry about the
4-wheelers around you.  I'm saying this for the non-rider's benefit.  You
already know.

If I was still riding, I'd have an IC706 or IC7000 mounted, along with the
dedicated dual bander.  In our area of the country, it is easy to pay attention
to what is going on around you and still play radio conservatively.  

As for rain, we didn't do much riding in the rain.  Sprinkles weren't a problem,
as the windshield took care of that unless stopped.  Covering it with the rain
cover used at night took care of it then.  Downpours usually meant we didn't
ride anyway, but the rain cover could still be used.

We pulled a trailer behind our XS1100 and our Aspencade.  Never once considered
not running mobile, but we didn't have small HF rigs available at that time for
a reasonable amount of $$.  :o)

I'd go with a good VHF installation and keep cell phones as a backup for out of
range conditions.

Gary - AG0N
Founder ARMC Net
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