I pay close attention to the NOAA operational wind forcast in my region. The page gives you an hour-by-hour wind direction display, which helps to set up my course for that day's sail. Typically, you want to "beat" on the way out, and cruise on the way back to dock. I prefer the 5-10 (light blue) and 10-15 (green) range, but tend to avoid sailing in my H27 if I'm looking at sustained 25+ winds.
Pay attention to flagpoles. Flags with no motion = bad. Flags waving back and forth = good. Flags starched = watch out. Flags starched and lifting up = fuhgitaboudit.
Our boats are pretty similar, and I suggest making sea trials in different types of weather and conditions. I don't take my family out when it's rough, but always find some adventurous souls. Even on a bad sail, you learn so much, especially what the boat can take. This year, I burried the rail twice (45 degree with this tank) on one of these shakedowns, and I was so concentrating on what the shrouds were doing, I hadn't noticed. What I did notice was water on the cockpit floor, and the concerned look on my 2 crewmembers' faces. They both said,"you didn't see that?"
"Ahwwww, man I missed it!" "Let's do it agian!"
"NO!" Mutiny.