We'll be doing the same trip the first week of August. You definitely don't want a full size on Black Bear, you would be fine with one on Imogene though.
Engineer Pass is another good choice, if you're into old mining stuff.
I've got my stock Rubicon sliders he's welcome to. They're butter than nothing, but not by much.
I'll agree with the above, the RSE slider with the step is not what he'd want. Without the step they're awesome, and substantially less than the Tera version.
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Yes, you received your bonus on your first run. And you two kicked butt! Hunter is one to watch out for in the future, and you're about to spend a lot of cash keeping up with him.
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