I've been wanting to hike up to the Hollywood sign since I was back in NYC, and with N's parents in town we finally decided to do it. We followed the directions in the handy guidebook Take a Hike and they were very clear and accurate. That book is a pretty valuable resource.
One thing I have to learn, though, is that whenever a guidebook lists a hike as "easy," that actually means "medium." In my mind, "easy" means "no effort whatsoever." But I guess that wouldn't really be a hike then, would it? It would be...a walk, I guess.
The Hollywood sign hike had some parts with a good incline to it, but the path was always flat and easy to navigate (no rocks or streams or anything like that to maneuver). The most challenging part was that there was little to no cover, so the sun just beats down on you and there's nowhere to hide. Every time we passed any patch of shade Stewie would immediately lay down in it.
Here's a view from behind the sign--this is the closest we could get to it; there are fences and motion detectors and supposed crazy amounts of security to prevent people form defacing the sign:
Stewie ended up getting the best view out of all of us at the peak: