My impression is that a lot of the begging has become like a job to Chris.
He is able to increase his income substantially by selling off a lot of stuff.
As is the case with most people who receive an increased income, he has gotten used to the increased flow of money, so he is not about to say "Ok thanks everyone, I have enough now."
In order to keep selling stuff, he has to keep marketing it. He understands that it sells for inflated prices because it is CWCabilia, so he doesn't want to just pawn it or have a quiet eBay store noone knows about.
Begging has become an integral part of his marketing strategy. For whatever reason, he feels like he needs to frame his sales in the form of charity. Like everyone else he has bills and financial obligations, so he can always say, without being entirely dishonest, that he needs money for bills.
Put that all together, and you get the result that the begging saga is fairly permanent. And, IMO, the only questionable part of his logic is that it needs to be framed as charity, and not just sold as "here is some stuff for sale, you should buy it if you want it." I don't know whether it increases his sales on net or not. It might get him the occasional pity sale from someone who doesn't follow things closely, but it might also drive people away who are annoyed. It might also help to keep his sales in the news, and provide more marketing. But it definitely pisses people off, and makes them feel like they have solid ground to criticize him for pissing his money away.
