While in a breakpoint during a XCTest (and later during a normal run), I encountered something... odd. I think the screenshot below explains my problem:
Why does it claim An Objective-C constant string's string initializer is not an array? It appears as if its attempt to translate my @"" NSString literal sugar into an NSString initializer-with-C-string was unsuccessful, but why?
Also, I've tested many other strings with the ¢ character or its Unicode escape sequence, and they all have the same result.

That looks like a bug. Please file it with http://bugreporter.apple.com.
Static string construction involves some compiler magic, and apparently lldb isn't getting that right when the string contains high-bit characters. You can achieve the same effect in the expression parser by using one of the NSString constructors:
Then you can use $newstr in future expressions.