Hi folks, so I'm currently rocking Pool of Radiance: Ruins of Myth Drannor on Crossover 18.5.0 and having a blast. The game runs great except for a few small bugs (not a WINE or Crossover issue, the game itself has some minor bugs that just didn't get fixed by the developers). I did use a few additional workarounds outside of just the base game, so I'll go ahead and list what I did to get such great performance.
Step 0
We first need to gather a few things, namely a copy of the game (I personally bought a used copy of the game via eBay for less than a Starbucks coffee, I've also heard that the game is available via Abandonware). We also want the official patches (versions 1.2, 1.3, and 1.4) as these squash a lot of issues. I would highly recommend checking Sorcerer's Palace (or a simple Google search) for these patches. Finally, we're going to need dgVoodoo2 Glide wrappers as these help the game run smoothly. Just Google "dgVoodoo2" (sans quotes) and it should be the first result you see. There'll be several different options, just download the one that says "latest stable version for regular usage" (v2.62.1 as of this writing).
Step 1
Install the game via Crossover. When prompted, choose the largest installation size possible (IIRC it's approx. 1.2GB) as we want all the files to be copied to the hard drive rather than the game having to read the disc (or iso) which will result in longer loading screens etc.
Step 2
Now that we have the game fully installed, the next step is to install the patches. First, download the patches as discussed previously and extract/unzip them (you should end up with a .exe file for each one). Then, from Crossover, right-click on the Pool of Radiance: RoMD bottle and choose the "install software into bottle" option. You can skip out on patch 1.1 as it's just an uninstaller (apparently back in the day, the game had a nasty habit of not just uninstalling itself but your entire Windows installation too lol). Choose the patch 1.2 exe file and follow the on-screen prompts. I personally had issues getting patch 1.2 installed (it kept complaining about "corrupt data"), your mileage may vary. After that, do the same with patches 1.3 & 1.4
Step 3
At this point we should have the full game and patches installed, but there's still one final step. We need the Voodoo2 wrappers as these help the game run silky smooth. Extract the dgVoodoo2 file and look inside it, you should see several folders: 3Dfx, Doc, MS, and a couple other files. Go inside the 3Dfx folder and then the x86 folder, then copy/paste the glide.dll, glide2.dll, glide3.dll files to an easily accessible location (downloads folder, desktop, wherever suits you). Next, go inside the MS folder, then the x86 folder, then copy/paste D3D8.dll, D3D9.dll, D3DImm.dll, and DDraw.dll in the same place you put the 3 glide files. Finally, we need to copy all these files into the Crossover bottle where the game resides. Open up Crossover, right-click on the Pool of Radiance: RoMD bottle, and choose "open C: drive". Navigate to where the actual game is installed (default should be Program Files/SSI/Pool of Radiance RoMD/). Copy/paste the glide/glide2/glide3 .dll files and the D3D8/D3D9/D3DI/DDraw .dll files here in the game's main directory where por2main.exe and pool II.exe reside.
And that's it! The game should run perfectly if you've followed the steps given. I've played the game for a solid 10 hours using the above setup and have been enjoying myself. The cutscenes work fine, I'm not noticing any artifacts or other anomalies, it just works. Now, where's my +3 orc-slaying axe??