Can you please reply with the Scheduler Engine log attached (they are in the same folder as those run detail files)? That will help me see what's going on. Look at your constraints. Are you specifying Sky Condition? What is the Sky Condition set on the Scheduler's window? If you can re-do this with the logging set to Debug, then attach that log it will help me more.

I can see you're maybe not using the web Astro-Imaging form. You might want to look at that as a really easy way to break your imageing into "chunks" to allow for scheduler flexibility. Separate topic though.