The stringification of sys.stderr is different in PyPy:
$ pypy -c 'import sys; print sys.stderr'
<open file '<fdopen>', mode 'w' at 0x00a42080>
$ python -c 'import sys; print sys.stderr'
<open file '<stderr>', mode 'w' at 0x10025a270>
The test will now ignore the exact value between the angle brackets.
The Windows-only wrapper around stdout is causing both of these tests to fail.
test-demandimport fails because it tries to print repr(sys.stdout). Use
stderr instead since that is not wrapped.
test-trusted fails because the wrapper doesn't handle softspace and an
unexpected extra space gets printed.