Hi Jake,
Will it be possible for you to do a screen recording of the issue you are facing and share it with us? It would be much easier to comprehend the sequence of steps that are happening on your machine. When DW is crashing, I am hoping that you are submitting the crash log along with your email id in the Adobe Crash reporter dialog that comes up.
You can also choose to send me the recording or crash log directly in a private message using the forum itself.
Thanks,
Arun