Guidance debugging broken application

[Xeno]

I am trying to get PWN Oxford 2004 working on Wine, but without success. According to the AppDB page, it can work, however that was with ancient version of Wine.

The problem is an error box, saying 'Unable to open file'. I have no idea how to go about finding out what exactly is going wrong, so could anyone give me a few pointers? I can get logs back if necessary.

[dimesio]

You didn't mention what Wine version you're using; if it's not the latest development release, upgrade. If it still doesn't work, run it from a terminal and post the output. http://wiki.winehq.org/FAQ#get_log

[Xeno]

I ran the application on Wine 1.7.11, and it still doesn't work. At first, it fails to load with DLL errors such as MFC_42.dll and DECO_32.dll, but I installed mfc42 through winetricks and got a copy of DECO_32.dll from a Windows machine. After those are installed (and a few missing libraries were installed - Linux side) the application got to where it was before, with a message box saying 'Unable to open data. Reinstall program'. No log output was seen.

I am running Wine on Arch 64-bit, with the aforementioned DLLs and libraries installed. Although the application doesn't install due to SafeDisk not working properly, I copied the program directory across from a Windows machine. In my previous attempts to find a fix I copied across all of the registry entries I could find referring to the application, but they do nothing.

[Xeno]

All I need is some guidance on how to go about finding out why this application isn't working. I have a little bit of experience with gdb, but when it comes to complex APIs (like Wine) and the extensive debugging framework, I have no idea. I'm assuming that the program is attempting to open something, and failing, and I need to find out what that file is and how to fix it.