Not at all Disney05...just tell the gate attendant that you're heading in for dinner. We've never had an issue. Although frowned upon, I have heard of non-resort people parking at a resort under the pretense that they're having breakfast, then grab the monorail into the MK or Epcot thereby avoiding the 14 dollar parking fee.

As far as pool hopping, I've done this several times, but as WDW1014 mentioned, you can't at Y&B's Stormalong Bay. The pool area is gated and only accessible with a key to the world room key.

My favorite resort to hang out at is the Polynesian during the evening hours. It's so relaxing to grab a deckchair and lounge on the beach or swing in a hammock. The grounds are lit with tikis so it's a great place to stroll as well. I believe Wednesday night? is their movie night and they set up a giant inflatable screen on the beach right by the water and have a fire with smores and everything. It's actually my favorite non-park way to spend an evening in Disney.