Who is Roland Orzabals Hey Andy?

Answer 1

I don't know if it was anyone specific, just the experience itself- Roland said in an interview that this song was him attempting to understand the deaths of some of the people close to him like his wife Caroline's father:

"It's difficult when people are dying around you. Caroline lost her mum two years ago, and her dad recently and although they aren't my parents, it does affect you, big time, especially when you see what your partner is going through. We lost our gardener, a good friend of mine lost his wife - a lot of death, I'm afraid. So you see with the lyrics, 'Hey Andy' - 'When I die you'll be waiting for me', I'm trying to gain some understanding of it."

(Sourced from http://www.sortedmagazine.com/Features.php3?nID=135) :)