Haven't watch this review that Bradon made yet but your game seems fun so im gonna play it!
Im gonna try to stick to your 4 man team as much as possible.
1)Long Driver: Musc Ravageur, It project, it last and it didn't get overpower in crowded places like family or friends reunion where there's perfume, food and a lot of different smells.
2) Short Game expert: Gucci Pour Homme II, you can wear it anywhere its not gonna bother or offense people at work or places like this, its stay close to the skin, smell great, very versatile, hard to over-apply, one of the best safe and versatile scent around.
3)Pressure Player: Musc Ravageur Again and Green Irish Tweed, One for colder weather and the other for warmer one. But Basically any fragrances im gonna name here qualifies for this.
4) Recovery Expert: For me its gonna be a mix of a comfort scent and one who lift you up or make you feel lighter. Gucci pour Homme II is the comfort one and Kenzo Power is the bright one who put a sunshine in the sky.
My Caddy: (The scent who didn't classified for this 4 roles but who deserve a mention) Dirty english, nothing sweet or unisex about this one, for when you need something masculin, manly but still modern and young.