More than once I've seen the existing functionality of an IDE's automatic (or semi-automatic) compile, run and debug loop sabotaged by some (sometimes mandated) third party plugin which is supposed to make things "easier." I've watched as people poorly integrate Java Spring into a project and render it impossible to use Eclipse's debug button because of badly constructed project dependencies. ("Oh, if you want to run the project, just drop into the command-line terminal and type 'ant someobscurebuildproduct run'; it's pretty easy, why are you complaining?") I've seen people integrate Maven into a build process in ways which guarantee the project will stop compiling at some unspecified time in the future by improperly scoping the range of libraries that will be accepted. (And I'm not a fan of Maven or CocoaPods or other external dependency resolution tools anyway, as in part it presumes the external libraries we link against that are hosted outside of our source kits will honor their public interface contracts as minor revisions roll out, something which isn't always true.)
I've seen refactoring which adds code bloat (rather than simplifies the code). I've seen home-rolled configuration files which make code discovery functions break code discovery functions in Eclipse useless (do you really need to home-roll you own class loader, and specify Java classes in JSON?). I've seen plenty of 'voodoo stick waving' standing in for good coding practices. I've seen the lava flow anti-pattern obscure a simple Java RTL call in 20 discrete layers of classes, each added on by another refactoring that did nothing but make things more obscure.
I've seen weird blends of ant and makefile build processes which took a product that should have taken perhaps 5 minutes to build take over an hour, and build processes so broken that it was impossible to shoe-horn into an IDE without rewriting the entire project. ("Real programmers use 'vi.'" *shakes head*)
In fact, I have a working theory about programmers--and that is this: Most programmers think something should be a certain level of difficulty. And when a project turns out to be easier than they think it should be, they add artificial complexity until it reaches the expected level of difficulty. At some point, the project then needs to grow, making things organically more difficult--but the artificial difficulty added by the programmer who thought things were too easy before then simply sabotage the project. This is why quite a few projects I've worked on over the past 25 years have failed.
This is why I have no hope for any project that attempts to fix the problem. That's because the problem is cultural, not technological. We've had IDEs which had integrated debugging and one-button build + run processes going back to the 1980's--yet somehow we always glom to the next big thing, oh, and sorry about breaking your IDE--but this next big thing is SO important it'll totally compensate for the fact that we broke your edit/run/debug cycle.
Meaning I guarantee you the moment someone builds a fool-proof IDE which makes it brain-dead simple to edit, compile, run and debug an application, some damned brain-dead fool will come along, worried that things shouldn't be harder, and break the system.