but am running into issues getting the images cropped to a size the wiki allows.
		
		
	 
Is your issue file size or dimensions?
Ideally neither causes a problem. You upload a pic at max quality/resolution. Then reference that file in a wiki page, which will automatically resize to your desired (or, wiki defaults) dimensions. 
The format to reference an image is 
[[File:[I]filename.extension[/I]|[I]options[/I]|[I]caption[/I]]] - the various options are described 
here. In most cases, I specify options of "thumb" and "300px" and the pic is perfect. 
For example, on 
this wiki page the top right pic was added with this code 
	
	
	
		Wiki:
	
	
		[[File:GSeries Family.png|thumb|right]]
	 
 
which auto-resizes the original pic to the size displayed. But click the image to see the original. You'll see a big image, and all resizing is handled by the wiki code, saving us humans the work.