1.5MB file: konigi-wireframe-stencils-2-0-11

30MB file: steamboat-potd-photos

150MB file: Appeared to work, but had to kill the upload cause it was interfering with my wife’s WoW raid.

Apparently the upload is governed by two settings in php.ini: post_max_size *and* upload_max_filesize. These need to be changed from 55M & 2M to 2000M respectively. The php.ini file then needed to be spammed across multiple directories in WordPress install due to how BlueHost is setup.