User blog comment:DragonbornMAGE/What our decisions really mean./@comment-98.67.155.3-20130626060121/@comment-4686961-20130626214816

The Thieves Guild are a great bunch of guys (and girls) once you get to know them. They're like family. Plus, when you complete the No Stone Unturned misc. quest, you will start to become obscenely wealthy. I can't even sell all my gems. I just buy from a shop, then sell him/her gems until they have no money (leaving with more money than when I entered). The major cash flow is worth being a little morally ambiguous. You kill more people joining the war (BTW, long live Ulfric Stormcloak and Talos be with you!).