Hi j.drake,
I read with pleasure that you want to run a poor man's install. I use mine for about half a year now exclusively as my main system and since hat have had exactly zero hassle with the OS any more Using a persistent home, I have customized every aspect of the OS you can imagine. I can absolutely recommend it, especially if you like to play around with the system and with unknown software a lot (as I like to do).
As for the boot, why don't you consider a boot loader? I prefer GRUB, you can set it up so that it boots Windows automatically after 1 second if you don't press a key at the boot. Also, it's extremely easy in GRUB to append the kernel options.
I gave up on booting USB devices, probably my hardware is too old.
probono