So what? If only successful managers are allowed to comment then we won't have anyone to comment on games or even for live commentary.
Pundits don't have to be successful managers just like how managers don't have to be successful players.
First of all lets make a distinction between posting on redcafe and sky football. The former is the modern equivalent of a supporter venting his views at a supporters club or at a pub. The audience is limited, everyone here accepts that none of us are experts in football and that some might have a bad day at the office. If things degenerate then mods would tackle it. Pundits on the other hand are being paid quite handsomely to deliver a well balanced professional view of things to a way wider audience. They are hired because of their past (ie you won't see Joe bloggs as pundit wouldn't you?) and therefore there is a certain responsibility towards the club that made them + their supporters not to sound too silly. That's because without that past and without those supporters they would be nobodies and they will return to being nobodies if they ever lost that. I mean would you hire someone as pundit whom even their own fans think they are stupid? I very much doubt it.
Now let me share something about myself. I was raised in a country were we were exposed to both the Serie A and the EPL. Having said that,we had free access to the Italian TV stations but not to the English channels. Which means that while we had to go to the supporters club to watch the game only for our relative to pick us up immediately after, we were fully exposed to Italian punditry of the late 80s and early 90s. The difference between then and now was that pundits of the time (at least in Italy) knew their limits. They would analyse and comment about the game in every detail (fouls, penalties, yellow cards, offsides etc) and maybe suggest substitutions but they would never trespass beyond those boundaries. Which made sense as pundits have zero idea what football management is and even if they did, they have no idea the circumstances the manager is living in at the moment. For example its easy for a pundit to suggest that United need to buy 2 CBs and then pin it on the manager or owners for failing on that but no one outside OT would know why such a thing didn't happen. Who knows maybe we're aiming for a big project (ex developing Carrington) which would mean we have to work on a limited budget. Else we might have tried 2-3 options and failed. Shit like that happens all the time. Therefore the problem isn't really about the class of 92 but more about people being paid quite handsomely, to talk about stuff, they have zero idea upon.
TBH I find the class of 92 to be lousy managers and pundits and there is a reason why. These guys were exposed to just 1 manager who happened to be a genius. Throughout time SAF sheltered them from the realities of football (ie bad CEO/shareholders, lack of cash flow which lead to difficult times, a falling out with the main shareholders, a hostile takeover etc) and kept them safe while he took the slack. All he asked in exchange was full commitment on the pitch like the foot soldiers they were. Which explains why they tend to be so idealistic as opposed to more pragmatic people like Carra who had to live under 4-5 managers who were nowhere near to SAF's level and therefore knows that football is tougher then the Nevilles portray it to be. Its not just the class of 92 tbh. Others who had a similar upbringing to them seem to share their very same flaws. Take Keane or Souness for example and you'll think that they spent their lives jumping from D Day to the Battle of Agincourt right to Stalingrad rather then playing football at some of the best clubs and the best managers of their era. What the feck they know about cash strapped clubs, lousy managers and lousy owners? Which explains why these guys fail big time when managing teams who are facing such circumstances (Sunderland, Valencia, Oldham)
Asking these people about their view about management is basically like asking a student from Eton to give their own solutions about knife crime in the some of the most socially deprived area. They have no idea of what they are talking about.