Setting up LMS on Windows Home Server (WHS)

I've been looking to get a Touch for the last few months to fill my Music jukebox requirement and despite the line being discontinued I am determined to go ahead as Sonos is too expensive and there aren't any other viable alternatives out there (that I know of).

I currently have an HP EX495 Windows Home Server v1 with ~250Gb of music on. I've been trying to update my collection to FLAC and am probably half way there.

Currently I don't have a itunes or Media Monkey installed anywhere and my music library is frankly a mess!

So I'm looking for advice on how to setup my music library ready for when I get hold of a Touch.

I've read about the LMS Plugin which I am aprehensive to install as my experience of plugins for the WHS has been poor with most causing the console to slow to a crawl. So I was hoping that people would be able to let me know what's the best way to run and install LMS on the WHS?

Also what would be the best software to manage the library and playlists with?

And how exactly does the library, LMS and MediaMonkey tie in together?

And where should I start?

Thanks in advance for any replies, I realise that my questions have probably been answered a million times before and are pretty basic. But my numerous searches haven't been very successful.