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Hi Ned,
On a brand new OS X Lion install with the latest XCode (4.3.2) and command line tools*, the following worked:
./configure --with-pydebug CC=clang MACOSX_DEPLOYMENT_TARGET=10.7
That is, everything built cleanly, and all tests ran without failures:
336 tests OK.
2 tests altered the execution environment:
 test_packaging test_site
26 tests skipped:
 test_codecmaps_cn test_codecmaps_hk test_codecmaps_jp
 test_codecmaps_kr test_codecmaps_tw test_curses test_dbm_gnu
 test_devpoll test_epoll test_gdb test_largefile test_lzma
 test_msilib test_ossaudiodev test_smtpnet test_socketserver
 test_startfile test_timeout test_tk test_ttk_guionly
 test_urllib2net test_urllibnet test_winreg test_winsound
 test_xmlrpc_net test_zipfile64
3 skips unexpected on darwin:
 test_lzma test_tk test_ttk_guionly
I presume the aim is to be able to build correctly (on all UNIX platforms) with just ./configure --with-pydebug, right?
How's your configure*-toolchain-fu?
Once we fix this I can add the build slave.
Side bar: note that this was a vanilla 10.6->10.7 install. The XCode 4.3.2 install on 10.7 was the first XCode ever installed on the box; there's no /Developer or any of the old gcc* cruft.
[*]: Went to https://developer.apple.com/downloads/index.action, logged in with my Apple ID, then downloaded 'Commandline Tools for XCode - Late March 2012' -- dmg was 'cltools_lion_latemarch12.dmg'.