What are the pros and cons of holding Company Command twice?

I don't know of a huge disadvantage, but I don't see an advantage to it either. I pulled two staff jobs, one l liked and one I didn't. S-1, the one I didn't, gave me the experience to answer a lot of the questions we get on this board, which shows the importance of the position. The other was Assistant Brigade Engineer, which was both fun and challenging since it's a Brigade Special Staff working directly with the S-3, so where the rubber met the road. Staff time is what you make of it.
If your job will allow it, I would try to pick up all those staff related schools and continue my education outside the military. Take a round out position somewhere. In todays climate, if you don't have an advance degree, you aren't going to be competitive when you hit the Light Colonel board.

I agree with CPT Cable, no particular advantage or disadvantage. I had 1 command as a 1LT and 2 as a CPT, doesn’t make me any more or less desirable for further leadership positions.
It is good for your career higher up in rank to be familiar with all the staff positions in addition to command because you could get thrown into any OIC position from O4 and up (without it being your branch).

Your own parking space?