For email, the main problem is the automating the public key management. There is some hope here in the deployment of secure DNS (DNSSEC), which has the potential to automate the process so that everyone, by default, has a public key without taking any special action.

However progress is extremely slow and the incentives weak, so I would be surprised to see significant progress any time soon for email.

If you use Skype (and probably other proprietary systems, even your mobile phone) encryption will probably come as standard. There may however be back-doors, possibly allowing the provider, governments and law enforcement access. But it's better than nothing. The architecture of Skype, where the traffic passes through completely untrusted super-nodes (for example my computer!) pretty much demands the use of encryption.