Really? This is your sticking point? All of the problems you listed have simple, easy solutions. First, solicit several female opinions on whether or not you look good in glasses. If people don't like your glasses, then either get new glasses or get contacts.
Use this (Okcupid's MyBestFace):
http://www.okcupid.com/mybestface
It's an easy way to figure out what pictures work better than others. Also, go out and take some pictures with your friends (preferably female friends). Read this article as well ("Don't be ugly by accident"):
http://blog.okcupid.com/index.php/dont- ... -accident/
-Wolf