Sometime last year I was on HostGator's VPS and WP Engine for several different sites. I was paying around $150 a month. HostGator started to shut me down for using too many resources and I was going way over the limit with WP Engine's 100k limit. I was fed up so I looked into Digital Ocean. I knew a bit server management but never really wanted to deal with it. I just wanted to produce content and make apps.

I purchased the $40/m plan on DO and started to move my sites over. In the process I learned a whole lot about configuring my own server. I got a pretty impressive setup going now and monitor it on New Relic. It really only took me a few weeks to learn everything and get all my sites stable. It's been several months now and have had to hardly ever login to my server to touch anything. Initially I was worried that I'd have to manage my sites and it'd suck up some of my time but really I'm actually saving time because I don't have to deal with HostGator or going over the limit with WP Engine. I'm saving $110 a month, I learned a whole lot in the process, and it really did not take much time to learn nor is it much of a maintenance at all to run.