UPDATE: I am made quite a discovery, was poking around a bit and decided I should try running the game with DirectX9 32bit exe, and surprisingly, the crash was no more - it worked! I was using the 64 bit one before.
Viewing post in Pirate Proposition bug
So far, the updates have been save compatible for about two years back. There is a method to synch up the save data for objects and things that have been added or need modification during the save-load process, so we've been able to keep old saves compatible for a long time, despite many content additions.