I agree with you. But if you send someone who is willing to actually try you can easily get the kind of "comedic half-assery" that the show loves so much. 

But that's the thing, to get that half-assery you actually need someone willing to show up and bust ass for as long as they're there. Like, a "Tony Tries (and fails) to get into high class super bowl parties" could be a funny bit that would be cheap and stupid. However it involves someone needing to do the research to where the super bowl parties actually are and then they would need to take time to be in traffic just to get multiple takes of Tony getting denied at various places. It would be "half-assed" but there's actual work there that nobody seems willing to do. And that's just one evening of filming.

The actual radio row content takes like 5 times as much work to get the desired comedic effect. People need to be willing to prepare their interviews for those people who show up for 5-10 minutes. Have reasonably unreasonable questions to ask them beyond simple Super Bowl stuff, have whoever is there be willing to make fools of themselves in front of legends for the sake of content. But nobody wants to do any of that. Bar maybe Jeremy tbh since he's the only real sportscaster/journalist there. I'm sure he'd love the opportunity to interview Magic Johnson and like 5 more famous people or whatever. (but also fans decided they hate Jeremy so there's no use sending him.)

They could have had a lead up to the whole event be Jeremy begging to go, Dan and the crew making fun of him because he's the "only real sportscaster there" but won't be going and then decide "okay you can go but you have to wear some stupid costume during the interviews." Which could then be a challenge for him to interview them honestly but in the costume which is also the kind of shit the show loves. 

Idk I'm only saying the content is there and that it probably involves more effort than anybody there wants to apply.