I assume the below is OK, but as I'm not sure I thought I'd ask.

I need to rent a car at an airport location and drive to a client site on a Sunday night. Booked the car Sun-Wed. The rest of my team arrives Monday afternoon. I now need to fly out Tue night to a second client and rent a car Tue late night - Thu but the team will need to take over my first reservation and return it on Wed. Due to the timelines and locations involved, it's not practical for the team to book a second car as they're arriving by Amtrak to a rural station and I have to pick them up. Our corporate contract does allow us to have other drivers so long as they are employees and licensed.

So the question here is should I expect trouble when I pick up the second car since I'm picking up nearly a day prior to my team returning my first? This schedule was not really what I intended, but is what I'm stuck with so I need to try to make something work to allow this.

Any experience with this? I've never had a need to overlap a car booking before.

No.
Nothing to worry about.
Been done many, many times ... plenty of threads on this topic, including this one from 2006.

Thanks, naturally I picked the wrong search keywords ...