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Technology
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It baffles me that companies the size of Microsoft can't nail UX. They have nigh-unlimited resources and just can't get software to work well in an environment that they themselves designed. I get that they will put the minimum amount of work into a product, so long as it's achieving it's goals, but companies this size have zero excuses for an app that doesn't work flawlessly.
Here's the thing - being bigger makes this much harder
Software is about vision - we learn methodologies and make all sorts of tools to enable collaboration, but one skilled and driven dev is always going to outperform a large team
It's a lot like painting murals. If you're making something big, you might want some helpers, but the painter is the guy with the vision, working on all the fine details. A few skilled people who have worked together for a long time might be able to do it together and you can make a design around the idea of collaboration, but generally you're going to get clashing styles