The smallest droplet is 5 dollars a month, do you pay 50 cents a month for your shared hosting?
>100x more in time
Have you even looked into DO or are you just making assumptions? You can create a ton of apps with one click (One-click apps) and install a full stack with WordPress, Drupal, Django, and much, much more, and it just works. If anything, it's the same amount of effort as some cPanel shared hosting.