If you consider Rupert a great Survivor player, you might feel, as I do, that he'll never win. He has too many friends to be successful.
Someone always gets screwed along the way. The last two great players to go far in Survivor (Brian/Rob C) had to keep their plans underwraps but they were still perceived as jerks.
Colby is the only person I can think of that had very few enemies, was a strong player and yet he still lost. I cannot for the life of me understand it. Rupert appears to be headed in that same direction, if he can even manage to make it that far.
One thing that has really disappointed me with the last few Survivors is the obsession to find the perfect person to take with you to F2. Maybe Jon really is a genius since he's proven to be a perfect person for that role. In a way, I kind of respect Burton for his plan to align the stronger players. Had he been able to do that without throwing a challenge, he may have been able to go far in the game.
Obviously I don't know what the problem is. It's a game involving humans with human qualities and human feelings. Too bad the jury is often so damn bitter.