Well, I've been riding for 40 years and have yet to experience anything that would lead me to carry the kitchen sink, certainly for your average UK audax.
Good point about not having shelter, but then roadside repairs can also be quite taxing in the cold and when you are tired.
Yes, each to their own. When all is said and done the possibility of a £100 taxi fare doesn't phase me that much when set against all the things I spend £100 on without so much as a thought
The other problem with trying on insurance is that you have to abandon the ride. Seems daft to do that for want of a chain tool or a tyre boot or whatever it is you’ve deemed too heavy to carry.
.
It depends on how much you value the ride, I suppose. At the moment I'm not riding much, but I did used to, and the more events I rode the less of an 'event' each one seemed. I'd add that I would weigh the thought of an abandon against carrying a chain tool on that ride, I'd weigh it against carrying every tool I'm never going to use on every single ride, if that makes sense to you. I prefer to maintain my bike really well at home, replace parts before they fail, and not get stressed about breakdowns on the ride or carrying tools for every eventuality.
I've had a chain break once in 40 years...and in truth I could have avoided it if I'd paid attention to a slight click and mis-shift that had been happening for the preceeding few days.