My little side project supports points 1 - 4. It has a neat disposable cover letter system built in.
I'll continue to slowly bootstrap MightyCV, it's a resume creation app with hacker leanings. It has integrations with HN, github and StackOverflow along with some other cool features. You can see an example of what one looks like here:
http://robeastham.mightycv.com
If you like the look of it you can sign up for a beta invite at:
I'm hoping to redo the management interface over the next few months and push out a largish update to the service along with some bug fixes.