Oh ya, frisco outer bar is intense. Its always so scary cause usually there is no one out when its that big. By far my worst paddle out was at duck pier when it was probably about 10 foot and heaving. The waves were so big they some were just cloudbreaking and washing through. Every wave was a massive barrel, but the paddle back to the lineup was hell. Also one time it was so big in VB that I paddled out in rudee inlet.
distance and difficulty are two totally different things - ocmd rarely ever has a long paddle compared to many other places but when it has any size it can be one of the hardest. I've been surfing oc and assateague for twenty years and ridden both in just about any condition we ever get, for both spots timing and picking your spot to paddle make all the difference in the world
You can almost always find a decent channel to get out at assateague I've been out as big as it gets and is still rideable and it's still a relatively easy paddle. That means try the same size/wind/swell direction elsewhere and it'll be way harder in comparison.
While paddling out at a beachbreak can be tough, reef breaks are much worse. There are a couple places here in Montauk where the bottom is rock reef, and when the tide is low enough and the water begins to recede you hear this weird growl. There's a field of rocks you have to navigate to paddle out, and if you don't time it right you get smashed and swirled around the rocks. And when its double overhead in early February, and you're wearing a 5 or 6 mil, booties gloves and hood, and duck diving is a bit harder, the pressure is really on not to get crushed. Those are the hardest paddles. As for longest, whether there's a current is a major factor. I hate when you paddle out through three layers of whitewater, only to find that you're a couple hundred yards further down from where you want to be. And after 15 minutes of fighting, you don't want to battle the current back to the peak. But its almost always worth it.
The paddle is all a part of the whole. It not only gets you in shape, it keeps you in shape, and don't you guys all use leashes anyway? Wow, what's this world coming to? That's why EVERYBODY goes to THE spot in mid-town because it's the shortest paddle around along with the Inlet. Suck it up- paddle, it won't kill ya.