The thing is that NSA has the ability to attack the infrastructure. If for example they can go to carrier providers and monitor the pipe no matter what we’d do on top of that would be futile. Furthermore, they can backdoor cryptography algorithms-which to my opinion is the scariest from all the revelations regarding NSA. So even if we move everyone to SSL we wouldn’t know if that’s enough.
The financial pain you’re referring to cuts both ways. If you were to boycott commercial solutions then you’d have to go and find alternatives. Which could be relatively easy for tech-savvy individuals but what about companies? They wouldn’t do it. Simply as that. No one would go out of their way to install an alternative to Exchange Server in order to put pressure on Microsoft. It’s not realistic.
Basically what we need is a new Internet. We have to change everything. I don’t know if that’s even feasible but my guess is that even if it was it will take a lot of time.