Image Upload question

Hello,

I’m currently looking to make a page where my client can log in, and in the post section, have an image upload box, allowing multiple uploads, then one displayed above the text included in the post.

If there is more than one image, I would like to have that one image click-able, which opens up a light box, and I can go through the sequence of images, like a typical light box.

Is there a plug-in that would work for my needs? I’ve been going round in circles all week experimenting with different CMs/Blog systems and can’t find what I’m looking for, so any help is appreciated!

Thanks.