As someone who works in the amorphous realm of "digital strategy", I was pursuing this exact "learning path" by deploying my personal website on Digital Ocean, where your droplet is a blank slate, and you have to configure everything.
Given the number of help threads and spotty documentation I had to look through to deploy a simple Wordpress site, I'd say it was more of a hassle than anything else. Unless you plan on doing this several more times, at which point you'd likely have worked the kinks out, stick with deepening your knowledge in an existing area of proficiency.
from Hacker News - New Comments: "WordPress" http://bit.ly/2KxaXtE
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