I don't know the exact details for your requirements but I would guess you should register your two drones as part 107 (meaning $5 each and different registration numbers) and then take the TRUST and you are free to check out roofs and other jobs...
Hi
I wrote a tool for this that is easy to use download and install to the set directory then just click the relevant button
https://github.com/Judslat/NewGimcal