Computer Audio – Help Getting Started

I want to add a computer based audio source. My goals are to store a majority of my music collection on a computer accessed hard drive (with back up) and have the ability to easily play those digital files through my main system. I would also like the ability to copy selected music from the hard drive onto a small portable hard drive (or a thumb drive?) so I can play it at remote locations such as an office system. I will consider playback hardware (DAC's etc.) at a later time.

Before I start ripping desired CD’s to my computer, I suspect I will need to first decide which type of computer and operating system I will be using (Mac or Windows). Since I already have a home desktop and work laptop that use a Windows based OS, given that I am not interested in i-tunes, and knowing that Windows based laptops are about half the cost of a MacBook Pro, are there any compelling reasons why I should consider purchasing a Mac over a similar featured Windows based laptop as a dedicated computer for my audio?

Once this first decision is made, then I am sure to have more questions about specific software I should use for ripping and playback to preserve the highest quality sound possible, hopefully to match my CD source components. Thanks for any help provided.