I have been using DO for a year now. When I started, I had no experience whatsoever with Linux (except that I had Ubuntu one installed on my PC), neither I really knew what was exactly a web server (I knew Apache by name only).
It is REALLY to set up a LAMP/LEMP stack with all the tutorials. They are very practical. Is is as easy as building Lego projects. So if you're planning to use your server for development purposes only, you will be good to go in no time, unless you are afraid of black screens.
Of course, things are more complicated if you want to use your server as production server. You will have to deal with security issues. Even thought security issues are covered in the tutorials, I think you will have to do some research on your own to know what menaces you are facing. But the tutorials are a good start.
You have (almost) nothing to lose by trying to manage your own server, but be careful if you plan to host production server. I would suggest to keep backups, and try to restore a droplet from them in case of something goes wrong.
If you need professional help for managing VPS please have a look at the VPS management plan