First: Freedome by F-Secure is closed source and there is no OpenVPN alternative. Always choose a VPN that has OpenVPN so that users can configure the connection to their needs. No need for this bloated mess.
Second: Whilst disposable Google accounts might seem like a good idea, there are any number of ways for Google to cross-correlate a disposable identity with your actual identity using fingerprinting captchas or even your screen resolution. Google does this to spot serial re-registrations and to stop people gaming Google Plus voting rings and spammers in general.
Third: Be careful of online websites offering fake-name services. Most of this data is generated server-side and logged for the purposes of cross-correlation with your IP address and useragent string. Quite possibly the vast majority of fake-identity sites are run by LEA
- I like to write some quick and dirty ruby gems to generate fake identities because then it can't be correlated. (The names are pulled in from disparate sources and I always ensure true-randomness).
- In terms of email, use things like Riseup which use TLS at every hop so that passive dragnets cant sniff the password. 99% of all IMAP and SMTP services can be passively sniffed because they use weak STARTTLS.
- Use 'honeywords' in an email to correlate different emails with different activities. For example:
john.doe+shopping@riseup.net
john.doe+gaming@riseup.net
john.doe+correspondant@riseup.net
This way you can whitelist those addresses for the purposes of filtering out spam and phishing attempts.