pouët.net

Is there a simple way to debug why a windows program I did crashes on Wine in Linux?

usually it's couz you're using newschool .dll's which arent properly supported yet.
sorry, don't really know how to debug it. have you checked their forums?

This might be the thing you're looking for: http://www.winehq.org/docs/winedev-guide/wine-debugger

Maybe it's easier to just implement a log on the target program, and add lot's of print points.

Most likely ;)