I was looking at the current implementation of SourceInitFile and there were a few things that made this function hard to read. The code to find the ~/.lldbinit file is duplicated across the cwd and non-cwd branch. The ./.lldbinit is once computed by resolving .lldbinit and once by resolving ./.lldbinit. Furthermore it wasn't clear to me what happened when you're sourcing the .lldbinit file in the current working directory. Apparently we do nothing when we property to control that is set to warn (makes sense) and we don't care when the property is set to true (debatable). Finally, there were at least two branches where the status of the CommandReturnObject were not set.
Anyway, this is an attempt to simplify this code a bit. It's still more complex than I had hoped.
Please let me know if you think it's more readable or not.