For "finding datacenters", traceroute is useful. You can just pick some websites and see where they host. For example, is seems that pinboard.in is hosted at http://he.net/colocation.html, Fremont 2, or at least that is where I am being routed.
I don't think he was making an argument for ease of maintenance, but rather, reliability per dollar. Even if you've got two crappy datacenters, you're at least redundantly crappy.
You need a capable sysadmin anyways. It makes sense to pay her/him to design and scale your "platform" properly, especially if you're making any money from it.
this is only useful for clients who aren't running their own switches & bgp. if they are running their own network, they can peer with ISPs that don't have physical locations in their dns names. this is a thing you can request, for obvious reasons.