It’s been a while since I have looked to see if a plugin like this exists. I found 1 that got close to it, but it was super clunky…

Having the ability on ay post, or page I guess, to be able to upload as many images as possible in the same fashion you would set a featured image. This way you get full access to the thumbnail sizes it generates.

So imagine just one of many scenarios, a portfolio post on some kind of project where you want to show off a bunch of pictures related to this project. You upload as many as you want and then in the theme’s code you are able to loop through images and do what you will with the raw image paths. This would allow the images to be used in almost any scenario. Slider, simple unordered list, etc.

Although the given scenario above would really only be useful for someone comfortable with theme dev. I suppose it could have some sort shortcode with some default markup resulting in an UL.

But anyways, I always thought this would be handy and have wanted to look into what it would take to create it myself, but who am I kidding, the time is just never there ^_^

Good luck, Michael!