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You can pickpocket everyone in the game if you need money. There is literally 100k in Neketaka alone worth of coins, gear and goods. Essentially, an unlimited amount of money available.

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On my first run I bought all the ships and the best ship upgrades and many of the best items (Falcon Helmet, Pale Hide, Dragon's Dowry...) and still had way over 100k in the end. At times I ran around with over 350k in my pockets. Once you start looting superb gear from enemies, you'll be swimming in monies. Of course this will become harder with increasing game difficulty, veteran was still a joke in the launch version.

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Generally, find kith and kill kith. Monsters drop junk, kith drop gear.

 

If you're an immoral sort of character you can also steal tons of stuff in Neketaka. I went with a goody two shoes character and didn't steal anything but I did unlock things for exp and had a peek inside, and left some solid stuff behind.

 

My next playthrough will be substantially more piratey I think, with more cheese because I'm going to build a hired adventurer party. I didn't get a lot out of the party banter this game. Eder/Xoti/Pallegina/Maia was my party, perhaps I missed out by not picking certain others but it wasn't as interesting as in PoE1.

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I started getting a lot of money near the end of my first playthrough from loot...but seemed like I always had something to spend it on.

 

The second playthrough has been a lot more fun with the 50k Blessing. Coincides well with the increased difficulty.

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Generally, find kith and kill kith. Monsters drop junk, kith drop gear.

 

If you're an immoral sort of character you can also steal tons of stuff in Neketaka. I went with a goody two shoes character and didn't steal anything but I did unlock things for exp and had a peek inside, and left some solid stuff behind.

 

My next playthrough will be substantially more piratey I think, with more cheese because I'm going to build a hired adventurer party. I didn't get a lot out of the party banter this game. Eder/Xoti/Pallegina/Maia was my party, perhaps I missed out by not picking certain others but it wasn't as interesting as in PoE1.

 

Hermit, I think that I'm thinking along the same lines as you.  My first character was a good and benevolent Fighter, and I didn't steal (or at least pickpocket) a thing.

 

But with my next party, my main character is going to be more of a piratey type, except I'm gonna stick with the Companions and Sidekicks.  The only thing is that I'm currently undecided what character build I want.  My first character was almost strictly a frontline tank, and after a while, I even had her give up any ranged weapons and filled all the weapon sets with different melee weapons.  I'm going to have the next character be some sort of ranged character.  I just don't know what class or classes I want, etc.  I'm also leaning towards making certain to have a very strong pickpocket in the party.  Maybe even in the main character.

 

The one thing that concerns me is how the companions will respond to a pirate flavored main character.  I'm sure that Serafen won't mind at all.  But everyone else?  I don't know.  If anyone has any experience with this concern, feel free to let me know.

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I haven't bothered with pickpocketing, as I found no issues with buying everything I wanted with $ from sales of items I didn't need...  But I heard you can pickpocket anyone with 2 points of Sleight, so maybe you don't need a dedicated character for that.  There are also posts on cheesing the stealth mechanic, through leap or conversations.  Mechanics (which should be in any party anyway) is probably the most intensive skill you'd need to have for looting chests.

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