Question
Is digitalocean beginner friendly?
If digitalocean will be my first host and I will use python django, flask is it a good fit.
Will I find it hard to manage services and upgrades myself?
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DO is like any other server.. In case of that, there is nothing which makes a service user friendly, rather its choice of platform, such as software and os you plan to use.
If you are good at linux and software you plan to use, then you get root access and you can do anything with it..
Secondly, hourly billing makes it really fun along with snapshot.. Create, play, if wrong destroy. You paid only for those hours :D
I concur with everything @hunky said, and will add that it might not be easy at first, but if you can stick with it you will learn skills that you can take anywhere.
In other words, DO is not some proprietary system. They use the most popular linux distros. If you can master your own server on DO, then you can set up and manage a linux server anywhere!
Does anyone use packer to create digitalocean instances and run them in vagrant so you can work at home the same as on the server?
https://packer.io/intro/getting-started/parallel-builds.html