I found a nifty plugin that partially serves my purpose; image upload and editing.
https://codecanyon.net/item/slim-image-cropper-for-gravity-forms/19606752
The only issue is that It isn’t equipped with the capability of updating/editing existing images. According to the author, it is due to a gravity forms limitation.
Does anyone know of an alternative ‘prepackaged’ solution that can handle both image uploads for new posts as well as image, as well as updates? A workaround that will add image editing capabilities (existing posts) to that plugin will also be fine.