Putting together datapacks is kind of a pain when I don't know why my new layer isn't being added. Please add more explanatory messages when a datapack fails to load any origins or a layer.

There should be sufficient messages for several cases. Can you please give an example of which error you ran into where the message wasn't enough to identify the problem?
Obviously, one reason for why your layer won't load is that it's either in a wrong folder, or the data pack isn't loaded. Origins can't detect anything wrong in that case, because it doesn't know about the layer file in the first place. If the console says "Trying to read layer file ..." though, you can be sure that Origins read it.

I see what you mean though. I'll make sure new features have sufficient error messages and also make the existing ones more failproof.