I found a solution/workaround for my problem. I came across [url=http://silverstripe.org/archive/show/250592]this thread[/url] which referenced the ThumbnailStripField.php file. This currently sets larger images to a width of 600 if its higher than that to work with the editor. I just changed that to 250 and huzzah, defaulting to 250! WIN!
Currently users are not able to specify image titles (for alt tag) in the CMS without going into the Files and Images section. We want to encourage users to add alt tags by having a text input box where they upload a photo.
Any help with that