|There is gold in them thar hills!|
In addition to these common trouble hotspots, I work in a creative led Digital Agency which, due to the nature of the beast, presents even more challenges around establishing dedicated teams with the right skill-sets, consistent delivery methodologies, adhering to best practices and educating internal and external stakeholders into rationale behind them. The last point around education is probably the biggest overarching challenge since if everyone knew what the right thing was to do, they would do it.
The best example of an education challenge is explaining the tax of distributed development. From a financial person's perspective distributed development is a no brainer.
"What? You mean one expensive onshore developer can fund almost five cheap offshore developers. These margins are massive! Well get on the phone to any country with a slightly f*cked economy and round up developers. Ideally it should be a country that has been oppressed by a communist regime guaranteeing optimal economic exploitation combined with a decent level of education. Yeehaaa! There is gold in them thar hills!" said fictitious Financial Person.