The drop rates for some items in this game are ridiculous.
Currently in Big Sky defeating Buffaloons and the drop rate for the item(s) to collect is ridiculous. It shouldn't take 30-40 battles to have an 1 item drop, this is just nonsense. This is also the case for a few other quests in this area.
As well, there aren't enough health fruit floating around.
Same with the notorious "holy water". Or "information" of Red Sash ships for "Are you chicken". The drop rate is also very low. Lower than 10%, so much I can tell so far. Still haven't found it and I do not consider that fun. Responsible persons, please try the missions yourself at the appopriate level with a standard boat. I am pretty sure, that you will adjust the droprate rather fast.
This has been noted elsewhere. Yet, when I asked support, I got the following:
"While this sounds more like a case of horrible luck, we'll send it up to see if there is any possible problem with the buffaloons dropping what they should be. Sometimes they just tend to be a bit picky, but keep at it and if necessary try taking a break from that quest and do some other side quests. By the time you return, it may just drop for you."
I did the math, and empirically it appears the drop rate is below 10% using the stats I know from available data...probably much below. Again, I like you may be having 'Horrible Luck', but after five hours of battles one would guess that mine luck is even worse than 'Horrible'.
So go to one of the cities in Big Sky and use the Life Fountain (which starts you healing) and grab their Yum Yum Fruit. If there are Treasure Chests that always appear in the approximately the same location, farm them also.
Make sure you are in the right area of Cool Ranch for your quest. Buffaloons seem to be found in all areas of Cool Ranch but the Quests specify which area you should use. Also check your map when you are in the right zone (area). It will show you where to find Buffaloons to kill. Finally use the Quest Arrow since it usually points correctly.
When I first came to Cool Ranch, I had to go back to town after every fight to heal. It does get a little easier, just don't give up. Don't expect it to be as easy as what happened before Cool Ranch. My current level 26 Privateer is still having problems, but he is now winning more fights without having to heal than he used to.