Why do I pay Linode $20/month instead of paying DO $5/month(1)?
Because Linode treats their servers like kittens (upgrades, addons/options, support), and DO treats their servers like cattle. There's nothing wrong with the cattle model of managing servers. But I'm not using Chef or Puppet, I just have one server that I use to put stuff up on the internet and host a few services. And Linode treats that one solitary server better than any other VPS host in the world.
(1) I do have one DO box as a simple secondary DNS server, for provider redundancy
Because Linode treats their servers like kittens (upgrades, addons/options, support), and DO treats their servers like cattle. There's nothing wrong with the cattle model of managing servers. But I'm not using Chef or Puppet, I just have one server that I use to put stuff up on the internet and host a few services. And Linode treats that one solitary server better than any other VPS host in the world.
(1) I do have one DO box as a simple secondary DNS server, for provider redundancy