Annual multi-trip or single trip travel insurance

Many savvy travellers assume that annual multi-trip travel insurance always offers a better deal than single-trip travel insurance largely because travel agents often charge ridiculous rates for single trip insurance. However, this isn't always the case. In fact there are many single-trip policies that start from as little as a few pounds. A good rule of thumb is that if you make more than two overseas trips a year (or one short-haul trip and one long-haul trip) you are better off with an annual policy as it will generally work out more cost effective. However, single-trip travel insurance is a good idea if you're only going to go away on a short-haul trip once or twice a year.
For those looking to travel to the USA, annual policies often work out cheaper than single-trip policies. This is because medical cover in the USA is high and so buying specifically for this country will increase your premium.