In the OP’s case he is in a different spot than a friend or acquaintance. I’m in the camp of no, as it doesn't take long to bang up someone’s siding brake. If it were a more rugged tool or less valuable I’d be more inclined to let it go and bug them every day until it came back.
As a rule I don’t loan stuff, but will come help and bring the tools if I can. If I do loan stuff the return period is pretty short before I become a pest. Most recently I let my 25 yr old son take my good drill, impact driver, and a ton of bits home for a project. He brought them back the next day….