I have no fear of climbing an extension ladder and stepping off onto a shingle roof. (as long as the pitch is not bad)
Getting off the roof onto the extension ladder is a whole other problem for me. The ladder always seems unstable (wants to slide)
I bought one of these last week and it's a game-changer. Solid, secure, and extension ladder makes it so much easier. It's basically a bar clamp with two grips....one for the gutter and one for the ladder. I have gutter screens and it works fine with those.
Available on Amazon.....
https://www.amazon.com/dp/B0CQGDK4QR?psc=1&ref=ppx_yo2ov_dt_b_product_details