Only if it could cost me lots of money. So my car is third party property only. So if I cause a crash, I could lose my car plus $1000 excess, but that's it, nothing that could ruin me financially.
For holidays, I try and book with a credit card that gives me travel insurance, but I'm really only interested in the medical insurance part. If I lost my passport and had to rebook flights, etc, it again wouldn't be a life changing amount of money.
Health insurance, yes, I've got decent hospital cover, but few extras.
I've got home and contents insurance for my PPOR as well, but I don't have silly things like pet insurance or anything of the kind. Nor do I have life insurance, if I die my fiance can sell all my IPs and have the PPOR pretty much debt free. Might not be as much as some other widows would get, but for a girl in her mid/late 20s, it's fine. I might change this once we have children, depending on the portfolio value then.