I am wondering if I should buy Redguard. I don't need help on what the features are, but if I would be able to play it. I know that if you use DOSbox there is a glitch in Clavicus Vile's realm that causes the game to crash. My question is, if I used a virtual machine for Windows 95/98 would this fix that glitch, because according to the UESP you must be on a "true" DOS or Windows 95/98 machine to play. Would the virtual machine help me? Or not? Thanks ahead of time.

Should work with VirtualPC or VMWare, I was able to launch it on VirtualPC once. I think I did not play far enough to know if it's definitely glitching out at some point, but after each crash I had I was able to launch the damned thing again and I actually proceeded, so it should be ok.

If you use a virtual machine, do not use VMWare if you have an alternative, I had very bad experiences with this product and Windows 95/98 (not related to Redguard).

I suggest you try giving the game a spin on Virtual Box. That's always worked great for me.

Would virtual box prevent the game from crashing at the part of the game with Clavicus Vile?

Sorry if I was misleading, but I wouldn't actually know since I've never played Redguard. What I meant to say is that Virtual Box has always worked great for me when I try to run fragile applications like this. At any rate, it wouldn't hurt for you to try it since its free software.

EDIT: Note that you will need a real, licensed copy of MSDOS or Windows 95 to play the game on. Virtual Box emulates entire computer systems, not just the OS. Alternatively you could use something like FreeDOS, which is supposed to be 100% compatible with all DOS programs (a claim which, being an ex-DOS programmer, I would testify to), but that might be even more of a fuss to setup than you'd be willing to deal with.

... man, this has gotten the inner IT-man inside of me curious. If I had a copy of Redguard, I'd love to try to get it up and running like this.

you may get performance issues under win95/98. If you dont install the glide version it runs poorly, if you do install the glide version and run at it over 1024*768 with real voodoo hardware it'll corrupt the on screen overlay, and slow cpu's ect will cause it to run in oversped bursts

For best results use (dual boot) windows XP 32 (NTVDM) and run DGvoodoo (Glide to DirectX wrapper), i was able to run it on my current processor with my old 6950 crossfire at 1600/1200 (make sure image scaling is disabled in your graphics cards control panel and on your monitor so it maps it on a 1:1 pixel ratio) with loads of supersampling and 16*anisotropic filtering, it massively helped smooth those old meshs and textures, it ran perfectly smooth aswell.

You'll also need sapucdex and VDMsound to complete the environment (CD and Sound)
http://www.uesp.net/wiki/Redguard:Installation_guide

It didnt suffer the dosbox issues of CTD when visting clavicus vile either.

also i used a PS3 controller to play it using http://www.motioninjoy.com/, there's probably one for Xbox 360 controller or another controller if you have one laying around

I've run it under win xp with dgvoodoo and didn't get the freeze issue.