I have all but tortured this thing figuring out where it is, and after running "\path\to\speccy\Speccy64.exe" /debug a lot of times, I figured out that it was the gathering of the OS data that was running into consistent, repeatable crashes. I don't know if it is on Windows itself or Speccy, and from reading the logs, I honestly cannot tell. I have a zip of a whole slew of logs, sorted into folders, attached to this post, and when I started reading through the OS ones, I noticed a trend: they ended in approximately the same place (3 ended at line 124 and 1 at 126) and the same step in the same process (at what is likely the end of getting a list of my several JREs, mostly from my JDKs). I wonder if there is a simple line that shouldn't be there in the code for getting the OS information. I did find that when I had every box except for the OS data analysis checked, it still never crashed, but when it only had that box checked, it crashed like clockwork.
List of logs.zip