The [imgur](https://github.com/kaimallea/node-imgur) API lets you upload an image (anonymously) and responds with a URL. I promisify'd that and the result is super straightforward. You don't even need to auth.
The Heroku deploy does appear to work, but I was hoping to get it all running locally. Thanks though! It looks like there's a ticket on the lwip project on github that is similar to my issue, so hopefully they'll resolve that soon enough :)