Princess Maker 5/Lip-sync
I hacked in a simple lip sync system into game. Characters can open their mouths while speaking now. But two frames need to be drawn for each portrait: with mouth half-open and with mouth open for it to work. This feature is off but default but can be enabled in Settings -> Lip sync. You need translation patch of version at least 1.1 for it to work.
Files needed to get you started: lipsync-1.0.rar
[edit] Adding frames
Game keeps portraits of characters in the face/bm directory. Format is Truevision Targa, but it is obfuscated in a very funny way to make it look life BMP. For that reason you can't just open these files in Photoshop. Download provided includes all these portraits in PNG format. Each needs three frames drawn: with mouth closed, half-open and open. They should be named respectively 1.png, 2.png and 3.png, and placed into translations/lipsync/{name of portrait without extension}/ directory. For file fa020no.png, for example, you must create these three files: translations/lipsync/fa020no/1.png, translations/lipsync/fa020no/2.png and translations/lipsync/fa020no/3.png. Usually, portrait picture will be the same as 1.png, the "mouth closed" frame, but in case where character has his mouth open in a portrait, you'll have to draw 1.png manually. You will find two sample portraits some kind soul already has drawn animation frames for: fa020no and fa020ki in the download.
[edit] Testing
One way to test lipsync-enabled portraits is to actually run the game and keep pressing buttons until you encounter the portrait. This can be very time consuming. I wrote a program that can preview animations, and it is included into download. To make it work, you place 1.png, 2.png, 3.png, and original portrait renamed to 0.png into program directory, and run the program. You then drag any sound file (.wav) from vo directory into program window. It will cause the sound to play and the character to move his lips in sync, just the way it would happen in-game.