Practice young padawan, practice ......
You're right though. I have been reading weather maps for years, first as a boatie and now as an astronomer. My weather patterns over here in NZ are obviously quite different from yours but I have taken notice of the TV predictions and watched the skies and now tend to make my own calls as to what will be good or not.
I go to my local weather map site daily and view the satellite pix, the infrared pix and the baro lines to understand where it is all coming from and what is likely to happen. Occaisonally I get it right ..
You will need to get familiar with what your local patterns are, they do recur, certain highs and lows will repeat weekly or seasonally. Do some research on weather and how it works with barometric readings etc.
There is no easy way, and the weather will always do something else anyway. Whatever you do, DON'T buy any new astro gear because the Cloud Gods will instantly change their schedule to ensure skies stay covered in direct proportion to the value of the new gear you have just purchased.
Guaranteed !!