I have never looked at the TTD exe, I don't believe there is much documentation on it even though I doubt it would help. I give in for now unless a dev can give me more sugestions on where to look and what to look for or tools to see why it crashes as I have no clue about debugging on DOS(Box).
Edit, I present a savegame saved on the 1st January 1932 the day before the crash. I may try and set it's date to a latter date, or even open it in OpenTTD.
Edit2, OpenTTD refused to open it.
Did setting it to a later date help?
Keep in mind, whoever achieves this will be remembered in the annals of history as the one who unlocked the Transport Tyccoon Prototype.
The one who blessed us with this fabled knowledge. Your Children will be proud of you for this massive achievement.
It will not be me, I can already say that, but it may be you. So do not give up, fight to achieve this, fight to unlock the Transport Tycoon Prototype!