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Anyone finding themselves trying to do something similar in windows, I created this guide (with images). It's still pending approval tho
Method for windows:
Required software: VirtualMidiSynth : https://coolsoft.altervista.org/en/virtualmidisynth#download
Steps:
1. Instal VirtualMidiSynth
2. Download Soundfont as above
3. Add soundfont to VirtualMidiSynth
Setting up OpenTTD to use the soundfont
1. Run game with command parameter: -d driver1
2. In the debug console that opens with the game, look for "Detected DirectMusic ports" and the list of devices below
3. Take note of the device nr of VirtualMIDISynth #1 [Emulated]
4. Launch game with command parameter: -m dmusic:port=X (where X is the device nr from step 3)
5. Profit
OpenTTD is poorly documented and I can't find any information if Windows build of OpenTTD supports FluidSynth in any way. On Windows, I would rather give it a try and replace default MIDI with an alternative driver. Look for a thread "How to install and set up Timidity++ driver" on doomworld forums. Timidity++ can play MIDI with soundfonts, and this project allows to register it as a Windows MIDI driver. There's a chance you will also need Coolsoft MIDIMapper to set it as default MIDI output device on Windows 10.