>It was a 5 foot ladder
Nope.
https://www.osha.gov/laws-regs/regulations/standardnumber/1910/1910.23
>For anyone to go on a roof takes very specialized training
Obviously you've never had a structure with a roof built.
Go to any construction site and count the teenage/twenty-something illegals hauling sheets of plywood, shingles and whatnot.
Sounds anti-Semitic.
>getting that in an out of a car
Only if your car is a TARDIS.
You'd strap it to the top, doofis.