Tie the trap via a rope to the end of the pole, then lower it onto the roof, and wait.
Or, bite the bullet, and pay a private service to come and get the poor thing. There are lots of contractors with "cherry pickers" used for stuff like tree-trimming, antenna service, etc. Probably wouldn't cost all that much, and there are far worse things to spend money on.
You can probably collect five bucks from half the people in the neighborhood to help out.
I just read your post...that’s exactly what I did. I made a pole, took my kitten trap, climbed the highest stair, and lowered it on the roof . The cat went in 7 times without stepping on the plate! It was unbelievable. After 3 hours 9:00pm the homeowners basically told me adios..goodnight..to leave. I went back this morning and the cat is not around..but I was told it never comes out in the daytime.....I bought some wood and am going to make a plank. IT’s about 30 feet high I figure...I have 45 feet of plank. If the cat is still alive and up there (it was VERY thin).. I just hope the plank works. I also showed a couple homeowners last year how to wrap up sloppy wet food with added water and pour it in a plastic bag and whip the bag up there so that it will open when it hits. It works great.(this has happened last year but that roof was alot lower and I was able to get a ladder up there and trap them and leave lots of water).... Just hope this cat is not too far gone. There are no hiding spots that we see yet this cat only appears at night and cries ALL NIGHT long. I’m waiting for a phone call from my friend to let me know when they spot it. I’ll put up the plank somehow. I’ll let you know how it goes.