Hi Holiday Matt,
you could try my new method.
Don't watch weather reports, do not check the cloud or jetstream forecasts on the IIS weather resources link, blisfully ignore the carpet of cloud or even occasional shower while you setup your scope outside. Decide you're going to get up and image something come hell or highwater, cheerfully drag yourself from bed and get setup all the while ignoring that cloud... and dang if it won't just clear right before your eyes, just as the eyepiec is slid into place. This has worked three time for me now in the last two weeks.
You just gotta show these weather gods that you're not to be trifled with
cheers,