Bashir's dad was interested in status so I guess failing was a problem to him. Maybe you just don't get to interact with people socially outside of your place in evolved society. So all his friends on earth are a bunch of other wannabes living in their boxes without groupies.
I don't think Earth is that crowded. A lot of the population died off in WWIII and it takes a long time to rebreed that many. I assume they have immigration laws still otherwise they'd be flooded with folk from shittier planets looking for their own box with a view of the park.
I bet the back to the land movement is huge with people growing their own food.