In order to ease "distant debugging" or "remote analysis", the best way is to instrument source code, I mean you should write logs of what is happening, especially during initialization phases in a dedicated log file on the hard drive. You would have identified all potential failed starts (when software just exits after a problem, such as corrupted file, ...). That way, it is much easier to diagnose what happens when software just refuses to start / shows weird issues. Easy to do, maybe time consuming to instrument source code if it is not done already, but very rewarding.

These are just my 2 cts.