Maybe you didn't have the same mods installed when you did it before..
There is a known issue on Windows 8/8.1/10 that it crashes a lot and is a lot less stable on those systems. Doesn't mean it can't run, it just means it won't run as well as say Windows 7 / Vista / XP.
Saying that, it is also a very bad PC port, as you may know.
You said it crashes on 'The Gym is Burning' which includes beta chracter 'Bob'.
You also mentioned you put leaders in freeroam. (Possibly by HxD?) Did you perhaps also put Bob into freeroam?
I don't know for sure, but if so, maybe that's what's causing the crash perhaps?
Try playing with a clean ide.img and see if that works, and then put your modded version back into the files after saving!
