Since this has all been addressed many times on this site, I'll be (uncharacteristically) succinct.
Travel insurance like World Nomads varies greatly according to where you buy it, usually your home country. That means anything I say about World Nomads or other insurance, including prices and what it covers, will be irrelevant unless you and I come from the same place. Which we don't.
For the most part, you need separate insurance in each country. There are exceptions, like the EU, the southern tier in South America, much of West Africa. And again for the most part, if you need insurance there'll be someone eager to sell it to you at or near the border.
Hope that's helpful. I'd suggest you continue to search the site, and continue to read up on the subject--the more you read, the more comprehensible it will all seem. You might also look at Chris Scott's books, or any similar books or online resources.
Mark
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