If your extension cord gets tangled up, don't pull on the ends. Instead, gently loosen all the tighter snarls in the middle until them become larger loops that can easily be untangled. A way to avoid tangles is to use a retractable cord reel. It will let you reel out only the amount of cord you need, then quickly reel it back when you're done.
When inspecting or repairing gutters, take the opportunity to attach narrow gauge chicken wire along the length of the gutters to prevent them from becoming blocked with debris.