Just get ready for a lot of downtime, conflicts, viruses, worms, malware and other problems with your Windows computer. I would definately buy an external hard drive for these files (which will make them easier to copy over anyway). My experience with Windows based computers is that to keep them working adequately (ie. half speed or better) I need to reinstall Windows at least once per year - wiping everyting on the HD out.
Apple to Windows...Questions
Currently running a 24" iMac bought new in 2008 and I've recorded a ton of LPs to .aiff files via Audacity which now reside in iTunes. Due to financial setbacks/major life changes I doubt very much that this computer system will be replaced with another Mac when it eventually fails. How seamlessly can I expect the transfer and utilization of these music files to be going to, say, a $600 (new) Windows machine? Currently I'm using a fairly basic wireless setup for music consisting of computer>Airport Extreme>Airport Express>stereo receiver/speakers in which iTunes is controlled by the "Remote" app on my cell phone. The info I've encountered via Google search thus far hasn't been fully explanatory...Any input/advice here would be welcome.