横からすみません、Macで同じ症状（system does not have PIL.）が出ているんですが、
ぐぐってみるとpydはWindows用Pythonライブラリとありました。
Macの場合、どうするのが簡単なのかしら……。
尚、現在はコマンドラインから「./tksaku.pyw」叩いて起動してます。
環境：MacOSバージョン10.6.6（MacMini Early 2009）
/usr/bin/python --version
→2.6.1
sudo port install py26-pil
→Error: Target org.macports.activate returned: Image error: /opt/local/bin/icc2ps already exists and does not belong to a registered port. Unable to activate port lcms.
----------------------------------------
Exception happened during processing of request from ('127.0.0.1', 39395)
Traceback (most recent call last):
File "/usr/lib/python2.6/SocketServer.py", line 560, in process_request_thread
self.finish_request(request, client_address)
File "/usr/lib/python2.6/SocketServer.py", line 322, in finish_request
self.RequestHandlerClass(request, client_address, self)
File "/usr/lib/python2.6/SocketServer.py", line 617, in __init__
self.handle()
File "/usr/lib/python2.6/BaseHTTPServer.py", line 329, in handle
self.handle_one_request()
File "/usr/lib/python2.6/BaseHTTPServer.py", line 323, in handle_one_request
method()
File "/usr/lib/python2.6/SimpleHTTPServer.py", line 43, in do_GET
f = self.send_head()
File "/home/hogehoge/shingetsu/LightCGIHTTPServer.py", line 115, in send_head
return CGIHTTPServer.CGIHTTPRequestHandler.send_head(self)
File "/usr/lib/python2.6/CGIHTTPServer.py", line 68, in send_head
return self.run_cgi()
File "/home/hogehoge/shingetsu/LightCGIHTTPServer.py", line 234, in run_cgi
cgiobj.start()
File "/home/hogehoge/shingetsu/basecgi.py", line 101, in start
self.run()
File "/home/hogehoge/shingetsu/client_cgi.py", line 124, in run
self.do_sync()
File "/home/hogehoge/shingetsu/client_cgi.py", line 188, in do_sync
cachelist.getall(timelimit=self.timelimit)
File "/home/hogehoge/shingetsu/cache.py", line 827, in getall
cache.search(searchlist=searchlist, myself=myself)
File "/home/hogehoge/shingetsu/cache.py", line 787, in search
self.get_with_range(node)
File "/home/hogehoge/shingetsu/cache.py", line 677, in get_with_range
count = self.check_data(res, begin=begin, end=now)
File "/home/hogehoge/shingetsu/cache.py", line 605, in check_data
for i in res:
File "/home/hogehoge/shingetsu/cache.py", line 447, in __iter__
idstr = h.strip().replace('<>', '_'))
File "/home/hogehoge/shingetsu/cache.py", line 107, in __init__
self.id = buf[1]
IndexError: list index out of range
----------------------------------------