People who understand that managing a server is a burden are precisely the people who should be managing their own servers, if only to help ensure the right and ability of people to continue doing so.
The more people flock to web services, the less demand and necessity for interoperability and standards, _especially_ for non-HTTP services. It's a civic duty to run your own services for those who are capable. Those who are incapable, but do so anyhow, will continue doing so regardless.
Also, I hate to sound like a fanboy but running OpenBSD is significantly less stressful than Linux. For many reasons (simplicity being the biggest, IMO), and particularly for basic HTTP, SMTP, and SSH services. Upgrading is more difficult than a simple `apt-get dist-upgrade', but I've done remote upgrades bi-annually for the past 12 years without a single problem.
The best system administrators are software developers, because the developers understand how crummy most software really is. But for this reason software developers hate doing system administration. It doesn't bode well for the security of any web service, where system administration and software engineering become highly specialized positions.