It runs quite well with CrossOver! So probably well with fine-tuned Wine settings as well :)

I remember it was challenging to install because I tried to install with the 3 disks and it still didn't work after. However I found a torrent of a "portable" version that worked out of the box!

Was the torrent a Wineskin?

No! It's a Windows torrent. I run Windows apps with CrossOver. The torrent name was "Dungeon Siege - Legends of Aranna + Return to Arhok + Yesterhaven [USBGaming.org]". Piracy is of course not legal if you don't own the original game (I'm not sure it is even if you do but meh).