Good news! This can be very easily done, Nate! In fact, I had to do the very same thing you are trying to accomplish with my church’s directory.
What I did first was create one entry which consisted of an image and a text box below it with the member information formatted the way I wanted it to appear. I made sure my text box was sized to the just fit all of my text (no extra space between the bottom line of text and bottom edge of the frame.
Next, I grouped my image and text box.
Then I created a text frame and sized it to fit my page margins.
Next step, copy or cut your one entry and paste it into your text frame. The grouped image and text box will now behave just like text! Voila! Simply copy and paste to create new entries. I split my text frames into columns as well, and in your case, looks like a two column text box will suit your layout nicely. Hope this helps! Good luck!