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> Why is that permissible but _PyLong_IS_SMALL_INT is not?
It's *permissable* primarily because it is there. There are many places in Python which invoke undefined behavior already (most notably wrt. signed integers); we should strive to eliminate them.
OTOH, obmalloc clearly makes a lot of assumptions on the hardware architecture (including the assumption that there is page-based virtual memory, etc). It's a memory allocator, that gives permission to make such assumptions. If it turns out that they break on some system, obmalloc cannot be used there - hence usage of obmalloc is still a compile-time option.
In addition, for the specific macros: it's easy to see that a compiler may optimize _PyLong_IS_SMALL_INT as true by simple static analysis. For Py_ADDRESS_IN_RANGE, the same static analysis is not possible, since the memory doesn't come from a declared array. It would require whole-program analysis to determine that .address always points to a memory block with ARENA_SIZE bytes. If a compiler manages to figure it out, obmalloc cannot be used on that system (and if that happens, I'll recommend to drop or revise obmalloc altogether, perhaps in favor of a system pool allocator).