aleigh
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It's not for-hire in your scenario, unless he has, or by agreement intends to, pay you for the service of transport. If you give me $2 for a $2 thing, or $2 for a $1 thing and I bring you the thing and change, it is not for-hire. If you keep the change "for your trouble", it is.
Providing transport for-hire doesn't automatically mean CDL though. For example, you can pay me to drive my car to the 7-11 to get you a slurpee. But not my LMTV.
I dunno about your guy or this guy or that guy but I don't think it's common experience that the DOT guys or especially the LEOs are well versed in any manner of the law other than that which they choose to selectively enforce - and interpret. Remember there is no one single version of the law. There is that guys interpretation of it. And then later the judges interpretation... And even that is not consistent necessarily from case to case. The law is fluid.
Providing transport for-hire doesn't automatically mean CDL though. For example, you can pay me to drive my car to the 7-11 to get you a slurpee. But not my LMTV.
I dunno about your guy or this guy or that guy but I don't think it's common experience that the DOT guys or especially the LEOs are well versed in any manner of the law other than that which they choose to selectively enforce - and interpret. Remember there is no one single version of the law. There is that guys interpretation of it. And then later the judges interpretation... And even that is not consistent necessarily from case to case. The law is fluid.