As for actually answering your question, I would go from low to high hit dice creatures, as I deem the vast majority of games will utilize lower hit dice creatures, while fewer games utilize the high level creatures. For instance most games will feature kobolds, orcs and goblins, while fewer campains will feature dragons and mind flayers. I also think that campaigns featuring high level monsters, often have lower hit dice monsters as minions, so again the low hit dice creatures would come into play So I would go from low to high, with focus on the classical monsters, leaving the more exotic monsters for later I was thinking something similar, so Orcs, Goblins, Kobolds, and each of their Chiefs, leaders, sub-leaders Shamen and other sub-races are all already programmed in the database. One of my group's DMs suggested a range of undead, so they're in there too. It does not completely fill all fields of the Character sheet (to reduce data size) but does the necessary for use in game. My data structures allow for inherritance of specifications from a "base creature", hence the families of definitions for e.g. all types of Orc, Kobold or Goblin. The complete list so far programmed is: Basilisk-Dracolisk, Basilisk-Greater, Basilisk-Lesser, Bear-Black, Bear-Brown, Bear-Cave, Bear-Polar, Beholder-45-49HP, Beholder-50-59HP, Beholder-60-69HP, Beholder-70-75HP, Blink-Dog, Brownie, Bugbear, Bugbear-Chieftain, Bugbear-Leader, Bugbear-ac5, Bullywug, Carrion-Crawler, Death-Dog, Elemental-Air, Elemental-Earth, Elemental-Fire, Elemental-Water, Ghast, Ghost-ethereal-plane, Ghost-material-plane, Ghoul, Goblin, Goblin-Chief, Goblin-Chief-Bodyguard, Goblin-Leader, Goblin-Leaders-Assistant, Goblin-Shaman-L5, Goblin-Sub-Chief, Goblin-ac6, Gorgon, Killmoulis, Kobold, Kobold+ac7, Kobold-Chieftain, Kobold-Guard, Kobold-bodyguard, Kobold-leader, Lacedon, Lich, Mummy, Orc, Orc-Bodyguard, Orc-Chieftain, Orc-Guard, Orc-Leader, Orc-Leaders-Assistant, Orc-Shaman-L5, Orc-Sub-Chief, Orc-ac6, Shadow, Skeleton, Skeleton-Animal, Skeleton-Monster, Spectre, Troll, Troll-Freshwater-Scrag, Troll-Freshwater-Shaman, Troll-Giant-Two-Headed, Troll-Saltwater-Marine-Scrag, Troll-Saltwater-Shaman, Troll-Shaman-Chieftain, Vampire, Wight, Wraith, Zombie, Zombie-Ju-Ju, Zombie-Monster