You might be more a half-full person, and I might be more a half-empty person. But I wouldn't call the (vaguely worded) legal restrictions on using licenses for binaries distributed by third parties, signing stuff with the wrong key, only supporting signing Win32 executables, "annoyances" of using an uncommon wrapper format, requiring Silverlight (plus basically Windows7) instead of a simple http upload, etc. "it evidently almost worked" :) Sure, not all steps are fatal showstoppers, but it looks to me that half of them could certainly be counted as such.
I haven't used Windows in the last decade (but I have dealt with certificates and signing, and it certainly doesn't have to be so painful), so I might be "out of touch" with how windows binary certification works. But I thought this whole process was for simple UEFI bootloaders to enable common hardware in the default setup and has basically nothing to do with Windows. Organizations that already use Windows anyway are probably not the target of this process.