Hours question... is this legitimate?

Being a company driver... If you're driving their truck and pulling their trailer and on your way to pick up a loaded trailer, that's log time.
Now if you were driving their truck with no trailer to their yard where you're going to sit and wait for a load, then it could be considered personal.
Any time the company tells you to drive their truck somewhere, it has to be logged.

 

Under no circumstance can you be driving off duty if you are hooked to a trailer.
Bob tail under personal conveyance means where ever you leave the trailer and go home, go to Walmart etc, is where you have to end your PC.
If they are asking you to pull an empty trailer then that's driving pure and simple.
If it's your dispatcher telling you to do this, I would March my backside right up to the saftey department to have a little chat with them.
If that didn't wake him up, I'd be on the phone with DOT.
If you do it, you get stopped, get into an accident, the dispatcher is going to tell them you made the decision. You really think he's going to fess up to telling you to blatantly lie.

 

Question 26: If a driver is permitted to use a Commercial Motor Vehicle (CMV) for personal reasons, how must the driving time be recorded?

Guidance:

a driver is relieved from work and all responsibility for performing work, time spent traveling from a driver’s home to his/her terminal (normal work reporting location), or from a driver’s terminal to his/her home, may be considered off-duty time. Similarly, time spent traveling short distances from a driver’s en route lodgings (such as en route terminals or motels) to restaurants in the vicinity of such lodgings may be considered off-duty time. The type of conveyance used from the terminal to the driver’s home, from the driver’s home to the terminal, or to restaurants in the vicinity of en route lodgings would not alter the situation unless the vehicle is laden. A driver may not operate a laden CMV as a personal conveyance. The driver who uses a motor carrier’s Commercial Motor Vehicle (CMV) for transportation home, and is subsequently called by the employing carrier and is then dispatched from home, would be on-duty from the time the driver leaves home.

A driver placed out of service for exceeding the requirements of the hours of service regulations may not drive a Commercial Motor Vehicle (CMV) to any location to obtain rest.

Their is not a thing about trailer in the guidance or regulation. Quit putting something in their that doesn't exist.

What is clear, if your working at the behest of your company, empty or loaded, trailer or not, you cannot run on personal conveyance.

 

Unless the empty trailer IS the load then you may use personal conveyance while empty or bobtail. The 2 things that for sure you can't do are use it while loaded at any time or while under dispatch. Everything else is kind of gray such as max distance or time, direction of travel, destination, etc.

 

This part seems to be summing up OP's situation quite nicely.

 

https://truckerpath.com/ = crystal ball