I bought the $1250 insurance, because I added an electric motor and battery to my bike. It is bolted in, so the whole bike needs to be stolen, and I hope the company will cover it (I sent in the $$receipt for the motor) and not call it an accessory. It is a risk about payout for sure.
I park in the suburbs, and only for up to 2 hours, outside of grocery stores, library fitness centres, errands, that sort of thing. Some have cameras nearby, and I look for lots of pedestrians to be around, so the lock attempt would not be for very long.
I keep my bike looking old, used, worn. The actual bike is 15+ years old and mid-grade, not looking fancy. Even so, someone did try to cut the lock on it as there is a lot of quick theft in the area.
I paid for 2 years coverage. After 2 years, I may not be using it as much, and will have gotten the $$ value from my motor kit.