Totally agree with cws. It's balancing the cost (and how much you can afford it) if it all goes wrong, the risk of it happening, convenience, and then building in some contingency that you're happy with.

I get decent travel insurance and check the schedules, I usually make sure there's atleast one more One World departure after my first flight which would comfortably allow me to make my connection. I personally err on the side of caution and sometimes this means an overnight stay in a nearby hotel.

I'm sure you will find others on here that aren't bothered about the cost, prefer the convenience and are happy to take fairly high risks of missing connections.