Need something that a technophobe could use to simply crop and resize images before uploading. Other options need to be kept at a minimum.
IrfanView is great, but there are just too many options.
Have you tried Paint.NET ?
It's often the perfect cross between MSPaint and Photoshop for me. It has basic support for a wide range of filetypes, and your basic drawing tools and image operations (resizing, cropping, etc.). It still has a lot of options, but it's free and feels like MSPaint, which I imagine the user is more familiar with than say, GIMP. For Crop & Resize, just tell them to ignore the Layers, Adjustments, and Effects menus.
All your technophobe needs to do is:
Paint allows you to very easily crop and resize images.
FastStone Image Viewer is a great image viewer and can do quick and simple crop and resize and a few other things. It's the best in this category and it's free. http://www.faststone.org/FSViewerDetail.htm