I migrated a number of my sites to Digital Ocean a few months ago. DevOps is definitely not my strong point, but I've learned a ton of valuable skills through setting up those droplets. It's also 20x cheaper than my managed hosting costs.

If anyone is interested in trying it out, I also wrote a pretty basic step-by-step tutorial: http://wptheming.com/2014/09/migrating-to-digital-ocean/.