A couple things that came to mind while reading the posts.

-Trevoke, you had me laughing with the Dr. Jeckly comment, I was thinking of Fight Club though

-Possible conduits into your machine for reinfection (IPOD)? Has storage capabilites. Are there any files other than music stored on it? Are there any other external devices such as Palms devices that you hook up that might carry a malicious payload?

-I read early on in the post someone asked if you updated the firmware on your router. I am not sure if you responded to that. Have you ever used a custom firmware upgrade on the router? I have seen quite a few out there and also read about some that are shady. Also, regarding the router, I know this sounds basic, but is it safe to assume you don't have the Remote Management option enabled?

-Not sure if you answered this, has anyone checked your female friends computer for infection?
What do you use as your mail client? Still use web mail? Outlook/Express? If so, disable the preview pane option. (thinking about the attacker using his female friends computer to send malicious files to him)

-I am most concerned that you said you run a web server from your laptop? What kind of web hosting do you do from a laptop? I think that needs to be investigated a bit more. What applications do you have running with the web server? (Shopping carts, add-in modules, applets, php pluggins) We had a client whose website got defaced due to not updating a PHP module/add-in, they reimaged the server, and loaded the same old version of php and didn't update it to the latest version as instructed, sure enough they got defaced within a week