@acavender did you consider just paying for wordpress.com as opposed to hosting it yourself, through digitalocean? I
When I started out, I had a blog on wordpress.com when it was still free (actually, I go back even farther than that — I started on Blogger).
I outgrew it pretty quickly, though — especially as I soon created my own multi-site network to host sites for my classes. I also ended up creating and managing a (now defunct) network for my college.
I don’t know if it’s even possible to have a multi-site network hosted by wordpress.com; if it is, I can’t imagine it’s affordable.
Self-hosting on DigitalOcean is less expensive than wordpress.com, where the $8/month plan doesn’t get me quite what I want in terms of control, and the $25/month plan gives me what I want, but also more than I need.
So in my case, the $5/month at DO is more sensible financially, and helps me develop some useful skills without being the pain to manage that WordPress can be. 
Hello
I have been looking into Medium lately. I have, from my perspective noted the positives of using Medium as your blogging platform:
I am now working on the negatives of choosing Medium. Any inputs will be appreciated.
Medium branding on my website is something I am not sure if I am comfortable with. It’s limited to the bottom of the page and on mobile, it gives you the option to open Medium app to read the article. I also think about that youtube does this too (and does not support custom domain) so perhaps I am being too precious and/or nit-picky