Man in the Middle Network Proxy for iOS that supports SSL?
Use mitmproxy. It's proven for this sort of thing. A while back there was some uproar about the app Path uploading the adressbook to its servers. This was what was used to discover it. The guy wrote up how he used it and that's a nice intro on how to install and use mitmproxy.



From the site :


  mitmproxy is an SSL-capable man-in-the-middle HTTP proxy. It provides
  a console interface that allows traffic flows to be inspected and
  edited on the fly.
  
  mitmdump is the command-line version of mitmproxy, with the same
  functionality but without the frills. Think tcpdump for HTTP. Features
  
  
  Intercept and modify HTTP traffic on the fly
  Save HTTP conversations for later replay and analysis
  Replay both HTTP clients and servers
  Make scripted changes to HTTP traffic using Python
  SSL interception certs generated on the fly