> So a client comes to you as a professional admin. Let's say they have > an aging Squeeze LTS based web server. They want to move to Jessie > which you may have heard is recently released. Would you re-install > their system to Jessie and ask them to reinstall their web site from > scratch? Or would you spend twenty minutes upgrading from Squeeze 6 > to Wheezy 7 and then from Wheezy 7 to Jessie 8? > > I would recommend they stop hosting their own machine and use a hosted service if they do not have a full time admin, actually. I generally haven't done work like that (freelancing or working for an integrator), but this isn't 2005 any more, either. Are there really that many companies - companies without their own IT department - with self hosted, unmanaged servers running around these days? Seriously?
And really, running a server on bare metal these days is a total waste. Any hypervisor will make remote work a lot easier, and avoid the whole issue with ssh and rebooting and everything else. Sheesh, it's 2015, ya'll. Sorry for the top posting.