Not a big entry, but when I initially installed WordPress I chose to use the catgeory tag when naming my posts. This is done in the permalinks section, and is a huge mistake. 

The permalinks category tag in WordPress is broken when it comes to using LINK TO PAGE as an option when uploading images. If you do use it the photo uploads without an issue and displays in the post, but when you click on it you get a 404 error. 

To fix this you need to dump the category tag in permalinks. 

I found the solution in the WordPress support forums after searching for 30 minutes. My search didn't have attachment.php in it.

So ... I hope this helps you fix the broken LINK TO PAGE ISSUE IN WORDPRESS.