Crash dump debugging is tricky to implement Python, because its normal debugging APIs - sys.settrace, frame objects etc - require being inside the process with a running Python interpreter.

You can still do it, but you basically have to redo the whole thing from scratch. For example, instead of asking for a repr() of an object to display its value, you have to access the internal representation of it directly - and then accommodate all the differences in that between various Python versions. Something like this (note several different dicts): https://github.com/Microsoft/PTVS/tree/bcdfec4f211488e373fa2...