I'm going to guess that WDW has lots of little policies they don't usually enforce but reserve the right to do so whenever possible. For instance, any Disney guidebook I've ever read-official or unofficial-specify that you aren't supposed to bring in outside food. However, plenty of people on this board will attest that they make up picnic baskets, store them in a locker and whip 'em out for a "free" lunch plenty of times. But if a loud, obnoxious and offensive group tried to bring in their own lunch, they could be turned away or asked to leave because that rule is in place. Personally, I'd think adherence to ALL the rules would be better for Disney so they could never be accused of being discriminatory. What if that loud and obnoxious family also happened to be black They could argue that, since other families had brought in food and weren't asked to leave, they were singled out due to their race. Disney could argue the case but it still wouldn't look good to see "'It's a Racist World' Sez Disney Clan" on the front page of the Sentinel, or any other paper that picked up the story.
Back on topic, and as has been previously stated, the only resorts that are connected by monorail are the Grand Floridian, Polynesian and Contemporary. If you drive to one (or get transportation to the TTC), you should be able to visit any or all of them as long as the monorail is running, but there is NO monorail service from the Hilton.
And brich, many homeless people find themselves drawn to populated areas. Some of them do so to become more anonymous, and anyone who ever lived in a huge city knows that it's easy to become that if you keep your head down and don't bother people. But others, who may want to get the attention of as many people as possible might find themselves drawn to WDW. If they are also mentally ill, they might also have a compulsion to be at WDW that goes beyond begging. The fact that you rarely if ever see the homeless or beggars at WDW might not be because they don't go there, but because WDW is efficient at ejecting them from the premises. Unlike, say, the streets of New York City, all of WDW is owned by a single corporation. They can eject you from anywhere on the grounds as sure as they could eject an intruder from walking into their corporate headquarters.
