You should definitely try again using an up-to-date version of python. CPython 2.7.5 was released in May 2013 and doesn't support https which is why you're getting that urllib2 error. Maybe the other errors will go away if you update too.
I dont know what the -DENABLE_DTRACE flag is, but i know DTrace no longer works on OSX 10.11 (if thats what you are running). Although I doubt thats the reason you can't compile...
The best method to get this up-and-running as soon as possible is to install the Anaconda package, which will keep all your stuff up to date, and won't mess with the system version of Python. If it doesn't run on Anaconda, I would be surprised..
EDIT: And for what its worth, I just installed cutadapt on CPython 2.7.10 via pip and it took a few seconds to successfully install, although I have DTrace enabled on my system.
Second Edit: I turned on DTrace restrictions and it still installed via pip. I think you just need the latest python and XCode, and you should be fine.