As CitizenFour pointed out, when it comes to online security, you have to balance the hassle you are willing to go to against a) how much you need or want to use that service, and b) what would be the consequences for you personally if security went astray. The answer will probably be different for everyone.
For instance, say you are punting in America, which is probably illegal, and you use a VPN to protect your emails; but then you are only 'half' protected if the other end doesn't use a VPN. Or even if she did you realise some VPNs keep logs so you could in theory be traced. So instead you use one of the commonly used referral services to keep your data secure and verify you to the prossie (as is frequently required). But then what if the referral service got hacked?
There is no such thing as total enduring online security. When Edward Snowden leaked the extent of government tapping of private data, he used the highest level of security possible to communicate with Laura Poitras, the investigative journalist who made the movie (and bear in mind that such things were his speciality); yet he himself predicted how long he would have before he was tracked.
For me, the hassle and penalty if caught punting in America is not worth it. The only time I think it's ok is down the hood where there's no checks and the warning systems are good enough mostly to stop you getting busted (added to the fact that the police don't really give a shit cos there's worse stuff to worry their sorry ass than some some damn prossie and her john). But for a nice civilised shag in nicer surroundings I'd rather jump a plane ticket than run the gauntlet and paying big bucks into the bargain.
You have to think, if AW got hacked, what would the hacker do with it? If your name's Prince Philip that's big time baby, but if it's Joe Blogs what Sunday Paper's gonna pay for that? Not meaning it csnt happen but get realistic over possible consequences and what it means to you.