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Group travel insurance or family+individual?

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I am very uneducated about travel insurance so apologies in advance...

We are booking a holiday for the autumn and will be travelling as a family of 5 plus my daughter's 18 yr old boyfriend, under the one booking.

Group insurance comes up much more expensive than getting a family policy and him to get an individual one (we can't get him in a family policy as far as I'm aware?)

I'm unsure quite how travel insurance works. If we were to be unfortunate enough to claim for the whole holiday, would this be possible if we booked family+individual cover?

Also, when they state max cancellation cover on quotes, is this per person or whole holiday?

Thanks
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