About one week in, and I've made a bit less progress than I had hoped. I sought out a server to use for hosting, and selected a host. The disappointment started with the sign up process, continued with the confirmation emails (requiring me to use their DNS servers rather than simply giving me IP of my box), peaked with being required to use FTP to connect to my server for file transfers (as opposed to SFTP, or FTP(S), FTP sends the credentials in the clear), then with an excellent close of a weak support system that double escapes so you're comments come through as "I\'m seeing lag...". Expect a post rating several different hosts in the next week or so.
Things are moving along on the local development, I've got the local server set up, with Windows Server 2008 on one partition, and Ubuntu Server Edition on the other, setting up the Windows partition however was not without it's failures.

I've started generating some performance metrics about the two different systems (static files, phpinfo(), phpsecinfo, etc. If you've got a particular application that I can have running with real-world data rather easily let me know) and should be able to start generating some nice graphs in the near future. Note that I don't expect IIS to be wining these fights, I just want to see what sort of metrics I should be expecting out of a server running IIS.
I will point out that to be fair, I used the apt-get install for php, and apache. This pained me greatly, I've been compiling apache and PHP from scractch, to have to use some sort of a pre-compiled distribution... it was like tiny daggers stabbing me from the keyboard with each key-press. I've got Windows Server set up with IIS7 & FastCGI support for PHP.