First thing.......
Hookup that trailer to truck ready to go and then measure the actual height from highest point on rig (usually the top of A/C unit). Do not just go by brochure/published height.
Use a long straight board and tape measure. Then you will know what YOUR actual set up height is.
Don't have an experience with laser devices for measurement.......don't know if they would be accurate with tree branches etc.
I am a decent judge of heights/lengths and just eye ball it. IF in doubt GF gets out and YELLS. Otherwise I just close my eyes and hope for best outcome.
One time in upper NY State we were on a transit road that connected with a one way road just before an overpass. As we came around the curve I noticed signage at overpass 12' 8" but it looked like we would fit. Bur I stopped and was going to try to backup into an area off road to figure out what we were going to do.
Several vehicles were in line behind us so as I walked back to ask them to back up/go around/gives us room a guy in a truck shouted out "Sign is wrong.....you'll be OK". He assured me that we would fit.
So I proceeded expecting to hear the crunch. Made it with inches to spare.
Guy pulled up alongside and said that the roadbed at been reworked a couple years ago and sign had never been changed.
My eye ball was right....but sign caused me to doubt.
Here are a few hand held laser distance measuring devices. A bit pricey but I guess cheaper than A/C replacement/roof repairs.
LINK