I was asked by my employer (mom and pop) to do a flight this Xmas. I guess the customer is paying decently. I am concerned about the practicality and safety of it. Its a photo flight of sorts. 

The job is to do a running landing at about 25 kts ground speed on the property owner's frozen over lake while he simultaneously drives a Ford Raptor (very nice custom) the opposite direction towards the sunset. He has arranged for a 21 gun salute right as the helicopter is about to touch down while the truck accelerates in the opposite direction. The truck will have a large USA flag in tow. Thing is the flag is like 20 feet high. He keeps talking about how the truck is short enough to drive under the rotor and that he wouldn't be "caught dead" having his "boys" shooting blanks so he is using live ammo. Should I do this? Seems really cool but still. 

Like a total wack job & Bull 💩! But then again it is a supposedly Robbie Ranger peelot too!!!

worst attempt I've seen in a while

The 21-gun salute seems odd, but what the hay? If the ice is thick enough to hold up a Raptor, it will probably support an R44. Figure out a way to do it safely, like not having the truck and helicopter paths come close, use camera angles to make it appear that they are. Be ready to pull pitch if it even looks like things aren't going as planned. Rehears in advance. Seems like a goofy thing to do with a helicopter, but people do goofy things all the time. Just don't do a goofy/unsafe thing. Have fun.

The union won't allow it.

Thanks for a real reply. It is for a commercial apparently. 

Keep in mind just because it's ice doesn't mean it's smoother than asphalt. Could be quite uneven, snow covered, Etc. Maybe keep it off the ground instead of running it on unless you know it's a flat surface. 

or call this guy since this is probably what inspired your tactical boss 

https://www.military.com/video/aircraft/helicopters/helicopter-goes-ice-skating/2920304601001

If it smells like a Shatsandwich, don't take a bite out of it.