Maybe on another level, some people may inwardly feel very proud about something they've done or something they own etc. , - nothing wrong with that - but they don't want to come off as arrogant or don't want the 'less fortunates' to 'feel bad'. So, they play this very elaborate game of the 'humblebrag' as you put it. They believe they can pull the wool over everyone's eyes. But, yes, it's pretty transparent sometimes. Doesn't bother me.