I think this plug-in is a good example of what we are (Aurigma team) moving to (one of our goals): we are making our products usage more simple that it is now. The first project was ASP.NET control when you could simply drag'n'drop it to the page, adjust its properties and ImageUploader insertion code created automatically. WordPress plug-in is the next step. You just copy its files to the plug-ins folder, activate it via administration panel and it starts working. What would be the next step? You could post your ideas about possible answer here.