Halfway figured it out. I guess I'll get the hang of thumbnails eventually.
The image uploader can act weird. I have noticed that when I try to upload certain orientation images from my camera phone they look squashed but then appear normal when you click the 'view full size' link.
Images loaded to comment replies and such can be forced to a certain pixel height/width after selecting the image you wish to load and then changing the px dimension on the uploader popup. Changing one of these values suffices in properly resizing your image as it defaults a proper scale up or down on the other axis.
Thanks, I did some better on my second attempt. What I really need to do is learn how to setup my phone to work with me instead of against me. I'll have to see about the uploader popup, don't think I have ever seen it.