Regardless of how well you plan there will eventually be weather that is local enough to not show up no matter what app you're staring at. Many years ago I set off from the Vista Point boat ramp at Jordan Lake in North Carolina and turned the tiller over to my friend. There was a tall cloud somewhat to windward of us and I knew we'd have to keep an eye on it. We sailed close hauled on a port tack (with the suspect cloud hidden behind the sails to starboard) in a lovely 10-12 knot breeze for 10 minutes or so on this hot summer day and then tacked. Upon tacking, we saw a skinny, cylindrical tendril sticking out horizontally from our suspect cloud with a definite fast spin around its long axis and heading right for us. My friend immediately abdicated the tiller (cause it wasn't his boat ) and I tacked again and sheeted the sails out for a beam reach and turned the boat to accommodate the direction of coming blast (I hoped). When it hit I steered to balance the boat as we popped up on plane. The next several minutes were the fastest sailing I've ever done, including my windsurfing days. The boat was rock solid planing on a beam reach but we were taking spray over the rail that resembled a fire hose. Fortunately the event was short-lived and we were able to gather our wits and bail once it moved on.
My point in telling this story is that it's fine to second-guess your choices of whether to sail or not in any given conditions, but you can't predict what's going to happen once you've made the decision to sail and you also can't necessarily rely on technology to tell you that fun weather is coming. Once you're sailing, you're sailing and if you've got a good boat and you're on your toes, you can hopefully sail your way through the local weather blip that pops up, the way Pete did. Sometimes you just get a downburst and you get to whoop and holler your way through.
Once you've pushed off from the dock, keep your eyes on the sky instead of (or maybe as well as) the screen.