Earlier quoted context omitted.
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…
Not to turn a Netlify topic into a DigitalOcean topic, but when you created your droplet did you select the pre-built Wordpress option? May have helped you a bit. (I used dokku-wordpress[0] on my dokku imaged server, personally.) -- 0. https://github.com/dokku-community/dokku-wordpress
On DO, I learned that you have to set up everything yourself, like SSH, Apache, MySQL, PHP, SFTP. I haven't found good documentation on how to set up a Git workflow from my local dev environment, so that's the next step. I have a non-database PHP site I plan to use for that.