OP here (I am answering this question after two years, the post made by Daniel Cerecedo was not bad at a time, but the web services are developing very fast)
After three years of full-time software development (with focus also on software architecture, project management and microservice architecture) I definitely choose the second way (but with one general endpoint) as the best one.
If you have a special endpoint for images, it gives you much more power over handling those images.
We have the same REST API (Node.js) for both - mobile apps (iOS/android) and frontend (using React). This is 2017, therefore you don't want to store images locally, you want to upload them to some cloud storage (Google cloud, s3, cloudinary, ...), therefore you want some general handling over them.
Our typical flow is, that as soon as you select an image, it starts uploading on background (usually POST on /images endpoint), returning you the ID after uploading. This is really user-friendly, because user choose an image and then typically proceed with some other fields (i.e. address, name, ...), therefore when he hits "send" button, the image is usually already uploaded. He does not wait and watching the screen saying "uploading...".
The same goes for getting images. Especially thanks to mobile phones and limited mobile data, you don't want to send original images, you want to send resized images, so they do not take that much bandwidth (and to make your mobile apps faster, you often don't want to resize it at all, you want the image that fits perfectly into your view). For this reason, good apps are using something like cloudinary (or we do have our own image server for resizing).
Also, if the data are not private, then you send back to app/frontend just URL and it downloads it from cloud storage directly, which is huge saving of bandwidth and processing time for your server. In our bigger apps there are a lot of terabytes downloaded every month, you don't want to handle that directly on each of your REST API server, which is focused on CRUD operation. You want to handle that at one place (our Imageserver, which have caching etc.) or let cloud services handle all of it.
Cons : The only "cons" which you should think of is "not assigned images". User select images and continue with filling other fields, but then he says "nah" and turn off the app or tab, but meanwhile you successfully uploaded the image. This means you have uploaded an image which is not assigned anywhere.
There are several ways of handling this. The most easiest one is "I don't care", which is a relevant one, if this is not happening very often or you even have desire to store every image user send you (for any reason) and you don't want any deletion.
Another one is easy too - you have CRON and i.e. every week and you delete all unassigned images older than one week.