DandG--I always book through "insure my trip", here on TTOL. We always book a comprehensive plan, which covers a multitude of things. You can compare insurance policies side by side, to see how they stack up. Insurance policies vary widely, depending on what you need to insure against. For us, I don't really care about the airfare, for example, as we usually book with FF miles and if we need to cancel, we can change the dates on them. Also don't generally get too worked up about stuff like trip interruption, baggage stuff, etc. For the hotel, if we're staying at Beachside, we figure we can hopefully work something out on that.
I am worried about BIG stuff--like medical evac and uncovered medical expenses out of the country. Medicare pays NOTHING outside the US. We have a supplement plan, but it only pays 80%, I also generally look for PRIMARY medical coverage, which means that they pick up from the first dollar (after any deductibles) and you don't have to pay UP FRONT, which you could have to do, if the medical is secondary coverage only. Often, that means that you have to pay it up front, and then wait (and hope) they will reimburse you, perhaps months and months later.
In your case, you probably will need to look very hard at pre existing conditions. Many policies do not cover them, if for example, you need to be med-evacked (sp!!!) out. Some policies will cover pre existing conditions, IF the policy is obtained within a short period of time from when you originally made any payment toward the trip. Insurance is a difficult subject and you need to make sure you read all the fine print!
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