If you are looking for travel insurance, the site World Nomads (www.worldnomads.com) may be of interest to you. They apparently offer travel health and other insurance for unusual destinations and long-term travel at competitive rates. I say apparently because when I tried to get a sample quote, I failed because I live in Quebec, and at present they don't offer insurance to residents of my province.
According to a note on the site, they hope to do so soon. At least they are better than the New Yorker (www.newyorker.com) which does not allow residents of Quebec to enter its cartoon caption contests and apparently has no plans to change this policy. I guess we would be treated better if we lived in Afghanistan, the Marshall Islands or some other remote place.
In any case, the World Nomads site also includes some advice on travelling safely and on a budget. One details the author's account of arriving in Nice, France without a hostel reservation and discovering that there was no place for him to stay. (Been there, done that, slept in the car.) He opted to join a group of fellow backpackers sleeping in front of the train station, and awoke to find that his pack and most of his belongings had been stolen. Luckily he had his passport and some other important documents in his pockets, and by searching the neighbourhood was able to find some of the rest of his stuff, including a Eurailpass.
He also offers advice on surviving the U.K. on a budget, surviving Amtrak and the cross-Canada rail trip, and surviving night bus trips. You will notice there is a considerable emphasis on survival in many of these posts, but then I guess insurance and survival are related topics.