I would suggest that you give a try to WYSI-Wordpress, which is a WYSIWYG text editor allowing you to upload images, manage them and put floating images inside your posts. If you are okay with a non-WordPress PHP classes, try phpThumb(), at https://phpthumb.sourceforge.net/, which uses separate calls from IMG tags – something like < img src=”phpthumb.php?src = image & effects=parameters” > The advantages of phpThumb is that it is separate image managing software, makes thumbs of images on local and even remote servers, caches them and applies huge range of effects (watermark image or text, rotating, shadows, blur, alpha, levels, gamma, etc.) To simplify usage of phpThumbs you might want to edit quicktags.js in wp-admin dir so your img quicktag create phpThumb() calls rather than standard img tags. On my blog I use WYSI-Wordpress which disables quicktags, so I edited the bbcode plugin so I use [url] tags instead (and with BBCode Firefox plugin, adding phpThumb calls is a 5-seconds effort).