by Ranior
The math is correct for those cases. Depending on the exact circumstances for hunting/whaling/trapping your chances of success are increased a bit. They tend to be pretty modest increases as your calculations show.Basically it's a good occupation, but it's not that great. On average I suspect it helps one succeed where otherwise you would have failed about once per game. On top of that it maybe helps you get a slightly larger tile once per game. Both of those things taken together are worth maybe 3-4 points, putting the entire occupation at about 5-6. That's certainly quite nice but is just a little above the average in my opinion.
Because remember the only way this is befitting you is if you actually fail or don't want your first three rolls but then somehow do like the 4th roll. You obviously don't get to see the result of all four rolls and then decide which is best. So for all those times you roll a 3 on your first roll and take it for hunting, you have no clue if you maybe would have got a 1 if you kept rolling. So the total number of extra die rolls you get off of Proficient Hunter likely isn't all that many anyhow.
Unfortunately I can't really help much with any math though for raiding/pillaging because it's hard to model that situation. But much like the above, you rarely are going to even be rolling the die a 4th time and even then you rarely are going to like the result of your 4th die roll.