Can a pointer (address) ever be negative?

The valid values for a pointer are entirely implementation-dependent, so, yes, a pointer address could be negative.

More importantly, however, consider (as an example of a possible implementation choice) the case where you are on a 32-bit platform with a 32-bit pointer size. Any value that can be represented by that 32-bit value might be a valid pointer. Other than the null pointer, any pointer value might be a valid pointer to an object.

For your specific use case, you should consider returning a status code and perhaps taking the pointer as a parameter to the function.

No, addresses aren't always positive - on x86_64, pointers are sign-extended and the address space is clustered symmetrically around 0 (though it is usual for the "negative" addresses to be kernel addresses).

However the point is mostly moot, since C only defines the meaning of < and > pointer comparisons between pointers that are to part of the same object, or one past the end of an array. Pointers to completely different objects cannot be meaningfully compared other than for exact equality, at least in standard C - if (p < NULL) has no well defined semantics.

You should create a dummy object with static storage duration and use its address as your unintialised value:

extern char uninit_sentinel;
#define UNINITIALISED ((void *)&uninit_sentinel)

It's guaranteed to have a single, unique address across your program.

It's generally a bad design to try to multiplex special values onto a return value... you're trying to do too much with a single value. It would be cleaner to return your "success pointer" via argument, rather than the return value. That leaves lots of non-conflicting space in the return value for all of the conditions you want to describe:

int SomeFunction(SomeType **p)
{
    *p = NULL;
    if (/* check for uninitialized ... */)
        return UNINITIALIZED;
    if (/* check for failure ... */)
        return FAILURE;

    *p = yourValue;
    return SUCCESS;
}

You should also do typical argument checking (ensure that 'p' isn't NULL).

The C language does not define the notion of "negativity" for pointers. The property of "being negative" is a chiefly arithmetical one, not in any way applicable to values of pointer type.

If you have a pointer-returning function, then you cannot meaningfully return the value of -1 from that function. In C language integral values (other than zero) are not implicitly convertible to pointer types. An attempt to return -1 from a pointer-returning function is an immediate constraint violation that will result in diagnostic message. In short, it is an error. If your compiler allows it, it simply means that it doesn't enforce that constraint too strictly (most of the time they do it for compatibility with pre-standard code).

If you force the value of -1 to pointer type by an explicit cast, the result of the cast will be implementation-defined. The language itself makes no guarantees about it. It might easily prove to be the same as some other, valid pointer value.

If you want to create a reserved pointer value, there no need to malloc anything. You can simple declare a global variable of the desired type and use its address as the reserved value. It is guaranteed to be unique.