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I just wish there was a content editor for GitHub a little better than http://prose.io/.

Prose is great, but not good enough for HTML, customization or other static site generators than Jekyll.

Agreed. Prose is a decent start, but could use some updating.
Have you tried netlify-cms ? I have been using it for my friends site and we both are quite happy with it.
Netlify-cms seems alright, deff pretty rough around the edges though. It could use some polish and some more features 100%
Thank you. This was a very good recommendation.
DatoCMS is really impressive, but the fact is developers usually only need a CMS for clients, and clients are going to raise holy hell if the commercial CMS you set up for them 2 years ago goes out of business.

So while all things being equal I'd prefer to choose the indie business, having been down this road before I am wary. Especially since the CMS is not a layer on top of git, so getting content out and ready for another solution will not be pretty.

I learned about Dato a while ago and was pretty impressed ever since. Unfortunately I don't really have a need for it right now as I rarely do that kind of client work, but if I was in such a situation Middleman + Dato + Netlify would seem like a fantastic combination.