Prior to the 2017 "Great American Eclipse", I made reservations at two hotels -- each within a day's drive of my location that were near the path of totality. I then built a screenscraper from one of the weather sites (WUnderground, IIRC) that took the cloud forecast for the eclipse and presented it as a time-series. (Yes, I knew there was significant uncertainty involved!)
About 3 days before the eclipse, I decided which site to visit and ditched the other hotel reservation.
It worked well. My wife and I each saw our first total solar eclipse!!!
There's one coming up in 2024 too. Maybe some enterprising soul would like to expand on the idea and create cloud-coverage forecasts for the entire path of totality?