@sagebrushfire : I'm using Windows Foms. I never tried WPF or Silverlight. As for how far we can take the generator, it is only a program to superimpose pictures. The way the generator is made, it is able to import RPG Maker's resources, but by default there is no resources included; doing so, it is not something that replace a functionality of RPG Maker, it is an additional program to create resources.
If you like making Windows Forms apps then WPF is worth giving a shot. Visual Studio Community 2013 and 2015 are free for personal use so there's no excuse not to upgrade and try some of the newer stuff. Silverlight doesn't have a bright future, which is sad because it's actually incredibly powerful but browser plugins are going the way of the Dodo.
Yeah I can see where a generator for the images can't really cause any issue because it's technically not specific to RPG maker. I was thinking something along the lines of a Switch/Variable/Event manager for those who aren't a fan of how those must be edited in RMMV and also maybe an alternate map editor that emulates the layering aspect that people liked about previous versions and seem to dislike about MV. But that's kind of the core functionality of the program itself so it's almost like making a whole new version of it.
Assuming you purchased the program legally I doubt they would care but I don't know how they'd feel about someone distributing an entirely alternate version of the program, whether or not it was free. All the same it seems like such a fun project.