Re: Devs in the house
I've heard CIOs express the opposite of what you describe Joe -- that once it's clear an application is going to be "a key driver of new revenue, would have a lot of customers, and would be something that was expected to be improved and updated constantly for several years", that's when they decide they need the development talent in house.
Vail Resorts CIO described this very scenario with its customer-facing EpicMix app: It started with outsourced web/mobile developers, but once the app was a hit, and they knew they'd want to add new features every year, they started hiring developers. And their approach to outsourcers changed -- they started bringing in the select expert talent they needed, and having them work on premises, in partnership with Vail staff.
Here's a link describing Vail's experience: