I was rather taken aback. It occurred to me that my shock might be because I am English; I am likewise a little disturbed at the custom of
We had Sukkah-hopping in England, but it was something else entirely. It meant visiting friends' sukkahs, and enjoying a snack in their company. But the numerous groups of kids who kept showing up over the course of Yom Tov to the home of complete strangers were not doing that. Kitted out with bulging collection bags, they were on a mission to obtain free sugary loot (especially the kind for which one is not even obligated to make a "lesheiv").
It became such an issue this year in Bet Shemesh/ Ramat Bet Shemesh that people were arguing about it on the local e-mail discussion group. There were those who said that it's a harmless way of helping kids enjoy Chag. Others said that they are glad to host children in their sukkah for singing, divrei Torah and friendly discussion, while enjoying snacks, but they will not give to kids who come with a collection bag to take treats away.
Personally, I agree with the latter. The sort of "Sukkah hopping" that we saw this year was no different from the Halloween custom of trick-or-treating (to which, incidentally, many in England objected when it was imported from the US). Usually, "trick or treat" does not involve a genuine threat of a trick; it's just a vague mention of one - just like "We're sukkah hopping!" has a vague guilt trip that for the sake of Sukkos, you should give candy!
But even if it's a bit of a stretch to view trick-or-treating, and sukkah-hopping, as mild extortion, it's certainly begging. There was a time when even some children once objected to this: for Halloween 1948, members of the Madison Square Boys Club in New York City carried a parade banner that read "American Boys Don't Beg." Today, with the decline of the work ethic, and the rise of the "I deserve everything" generation, this is particularly problematic.
The harm of teaching kids to beg is even more problematic in Orthodox Jewish society. In the last few decades, we have witnessed the rise of the charedi belief that it is normal, legitimate and even preferable to not work for a living, and to instead depend upon the community to support private study which is not directed towards serving any communal purpose. This is notwithstanding the fact that it goes against explicit directives of Chazal (e.g. that "it is better to flay carcasses in the market than to rely upon the community for support") as well as going against the much-vaunted "mesorah" (in which the mass kollel phenomenon was entirely unknown until a few years ago). A recent article in Ami magazine interviewed a "radical" member of the Israeli charedi world who said that the way of "true Judaism" is to combine work and study - for those who lack the aptitude or the motivation to study and cannot make it as full-time learners!
The way of "true Judaism," as described by Chazal, is that it is shameful to beg for our needs and desires, and to expect people to give you something when you are giving them nothing in return. So if your kid comes to my door and wants to share the joy of Sukkos, I'd be glad for him/her to come in to our Sukkah, have a snack, make a berachah and talk. But no collecting bag!