One thing you have to consider with only one on the island, don't you think you might get tired with the same overall feel to an album like Dark Side? It was on the charts for so long because it was considered one of the top "mood" albums for stoners ever created. I didn't mention whether you had some mood altering substance along for the trip but getting the munchies on a deserted island is not my idea of a party.
The problem with Dark Side was I went though too many albums. You get lit in a dark room with that and every crack, pop and surface hiss sounds like a foghorn. When that came out on CD, that was an immediate purchase.