It's possible, my friends...
Here's my original guide:
http://www.iplounge.net/forum/viewtopic.php?t=1624
But I'll paste it here anyway incase anyone wants Ubuntu.
Well, I managed to actually pull this off - EP and everything.
I'm running Ubuntu Linux 9.10 (Karmic) and I was able to run Mixer, IPL, and HS without much trouble. Here's what i went through:
1) I downloaded PlayOnLinux from their website (latest version, not one in channel). This is Wine with added functionality for playing Windows games. I set WINE with winecfg to emulate a desktop (1152x864) and to be Windows 98.
2) I followed this tutorial (http://www.smokinglinux.com/gaming/play-your-windows-games-with-wine-and-directx), and I skipped the part of copying the DLLs from a Windows installation.
3) I used a tutorial actually used for installing Word 2007 on WINE, but the things it told you to install seemed relevant. http://wine-review.blogspot.com/2009/11/office-2007-in-ubuntu-910-with-wine.html
4) I mounted NFSHS.ISO in my home folder\Virtual CD Drive\
then AFTER it was mounted, I set that to WINE's D:\ Drive.
5) I opened my virtual disk of HS, then ran SETUP.EXE with WINE. I followed the install instructions, leaving all to Default, except I chose a Full installation.