I've just uploaded a fresh Showakse v1.7.6 site and checked the multi-image size functionality. It seems to be working OK for myself.
Here's what I did:
(1) Site -> Customize Viewers -> Juicebox-Pro (Edit)
(2) Selected 'Large images', 'Medium image resize' and 'Small images' checkboxes.
(3) Created a new Juicebox-Pro gallery page (on 'Pages' panel).
(4) Clicked 'Upload' tab.
(5) Uploaded a single image (dimensions 4416 x 3312) via upload module (via HTML 5 method).
(6) Published site (clicked 'Publish').
(All image sizes and all other checkbox were left at their default values.)
Now, when I check inside the Juicebox-Pro gallery's folder (in the root Showkase directory), there's a folder named 'images'.
Directly inside this folder is the medium image (dimensions 1024 x 768).
Also, inside the folder is a subfolder named 'large' which contains the large image (dimensions 1280 x 960).
Finally, inside the folder is a subfolder named 'small' which contains the small image (dimensions 800 x 600.).
It is worth noting that Juicebox-Pro uses the medium images for a gallery being displayed on a desktop monitor (no matter what the size of the monitor is). Large images are reserved for when an image is opened in a new tab (via the Open Image button) or downloaded (via the Download Button). Small images are used on mobile devices, though (unless a retina/high pixel density screen is detected, in which case, medium images will be used).
Give it another go and hopefully it'll work OK for you as it does for me.