I know this is a small part of your post, but I wanted to highlight something about that episode I found incredibly interesting from a sociological/psychological standpoint. There were at least five (5) types of personalities/responses to him really worth looking at:
(1) the posters who are friendly and say, "congrats on the new condo, bro";
(2) the posters who are curious and ask legit questions about the area/building/etc... ;
(3) the posters who are doing well enough in their own lives, but simply aren't interested enough one way or another to comment (positive or negative) because that's not how they access/utilize CIS;
(4) the posters who live in their mother's boyfriend's basement/trailer/garage and can't help think SWFL is bragging about paying cash for his condo so they respond from a place of jealousy; and
(5) the posters who will take every opportunity to **** on SWFL no matter what because what they like most is bringing other people down.
It would be beautiful if CIS was full of people in the first and second categories, but still a marked improvement if it was mostly comprised of people in the third.