[NSFW] path difference in uploads folder?

Can you post a real sample, like the actual url?
It could be your theme, try switching to the 2012 theme to test.

Sure — first link is a bit NSFW.

https://cameraclubny.org/ccny_blog/
and
https://cameraclubny.org/ccny_blog/2012/12/17/happy-holidays/

Ok,
so on the home page you have images with their source set to :
wp-content/uploads/2013/01/ELIZABETH-RENSTROM_1581.jpg
and on the sub pages such as this:
https://cameraclubny.org/ccny_blog/2012/12/17/happy-holidays/
the image source is set to:
wp-content/uploads/2012/12/IMG_7782-copy.jpg
So the images are always coming with the same path.
you must then have an error in your system set up.
My guess is that you have the WordPress installed in the folder https://cameraclubny.org/ccny_blog but you probably have your WordPress Address (URL) and
Site Address (URL) set incorrectly. In your case they should both be set to: https://cameraclubny.org/ccny_blog

If this is not the case, and the change does not fix your issue, try switching to theme 2012 and test. If issue is fixed, then your theme is the problem. Most would normally display images with the full source path including the domain. ie: src="https://www.domain.com/install/wp-content/uploads/2012/11/image.jpg"