I posted a question to a different forum and it appears that WordPress is lacking in the ability I requested:
I would like the ability to do the same thing that the table with caption (see 1tess's comment towards the bottom of that thread) example allows me to do, but with built-in WordPress image insertion tools (no HTML or CSS) editing required.
Basically, I want the ability to add a couple of pictures (with captions) in a row and then have a line break after that w/out using the HTML editor). Even using the HTML editor (without the help of tables) I cannot use the caption shortcode along with an image and get this basic functionality to work. So far the only thing that seemed to allow me to do this is using a table, or, possibly, editing the CSS.
The blog I need help with is rachelprickett.wordpress.com.