The best place to train cutlass doll and dagger is with the 2 stumps inside the cave on cutthroat island. If you can attune both you can get 200 reps a go (although be prepaered to maybe die once or twice if you havent got lifedrain!!! LOL) but it is still possible to do with a smaller doll.
Then when your doll is maxed and you've got lifedrain using your cutlass will get you about 70 reps per stump. Dagger is a little dangerous under lvl 10 but u can always whip out ya doll and use lifedrain if health becomes low or remember to bring LOADS of tonics LOL.
Grenade works well on Kingshead as you can hide behind the fence and throw to yer hearts content at the bunch of 6/8 navy on the field.
I haven't found a great place yet for staff but if anyone else has please let me know.
