As a native New Yorker, I've gotten off pretty light in terms of having to deal with Penn Station. I'm talking, of course, about the current incarnation of Penn Station, and not the splendid cathedral of modern ingenuity and transportation that formerly stood in its footprint. By all accounts, the contemporary Penn Station is a deeply unpleasant and ill-conceived shadow of what it was and what it should be.
Like I said, though, I get off light. I only find myself darkening its corridors once a week or so during the summers, when I'm trying to hop a train out to my mom's place on Long Island, where my wife and kids are sequestered in July and August. While it's still a lame experience, at least I don't have to deal with it every day.
Many, many summers ago, I spent a good deal more time in Penn Station when I was working as a dishwasher at Ina Garten's Barefoot Contessa in Westhampton Beach (don't bother looking for Ina there now, she's long gone). I used to continually bounce back and forth between there and the city, which found me regularly racing through the congested and airless rabbit warren that was the Penn Station of the mid-80's (a pointedly less pleasant place than the one of today, I assure you).
There also used to be a massive video arcade in the bowels of Penn Station in the early 80's that I'd frequent called Station Break. Access to that arcade's diverse selection of games made dealing with the hassle of Penn Station worthwhile, but that was a very different era as well.
In any case, there was a great report on WNYC this morning about the abject shittiness of Penn Station, along with some great tips and bits of trivia about navigating the place with a modicum of stealth and efficiency. Check out its accompany article (and great video) by clicking on this link here.