I used to be an active contributor in Lonely Planet's Thorn Tree discussion forums. I haven't written anything there for years now, but I still occasionally check it. It's a good place for finding / asking info regarding small details about your destination: local timetables, opening hours, bank holidays, if a particular hotel is as good as they claim they are and such.

Regarding health insurance abroad, mine comes bundled with my homeowner's insurance policy. For several years I went with a pay-as-you-go system, bought from the airport on departure. The one I have now has better coverage. For the annual cost of maybe 1,5x single PAYG for a short trip, I can now travel practically as much as I like. Goes without saying, now when I have the good coverage, I don't get to travel so much anymore.

--J