Just general feedback:
Living in the USA, the only insurance I've bought has been appropriate health insurance. I make sure it covers me for where ever I am going -I figure I can get over the loss of a bike, but not a life changing injury or death! Though I know other countries I've been to have some form of universal health care, from a moral standpoint since I don't live in that country nor pay the taxes, I don't see why another country's tax payers should foot my health care bill if I need medical services. I figure health insurance costs are just part of touring -if you are not covered by your own country or as an individual where you plan to tour and if you can't afford health insurance, then you shouldn't be going unless you have your own private funds to cover large medical expenses. Of course if that country has no medical services to speak of, that doesn't apply and in which case you take your chances being aware of this
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I have never bothered with property insurance (though I may well be covered on my home owner's insurance, I'm not sure) as I feel that a catastrophic loss of all my touring possessions can be eventually replaced. As I've not been on a RTW trip nor am likely to, the word "eventually" is probably more acceptable to me. A couple of things make me think this way:
1. Any equipment loss is likely to be via the airline and hence I know I'll probably be able to get some money back (I realize there are small limits, but still it can be worth it if successful). I'm also pretty careful with my bike and stuff when I am on tour, so I think theft is less likely.
2. I have a backup bike and equipment if I want to go touring again.
3. Each time I don't pay it, I get ahead of the game.... (yes, I know I've been lucky).