This season is an object lesson in not allowing a team to get too old. You avoid that by being very selective about who you carry into their 30s. Given Thiago, Henderson, Fabinho, Salah, Van Dijk we can't be paying top end wages on another 30+ player well into their 30s. So yes, extending him would be pretty idiotic assuming he's not going to take a colossal pay cut.
Aside from Hendo, I'm not really seeing this major drop off from the other players. I mean Fab is 29, I think we're starting to go a little OTT with what ages we should be getting rid of players.
Alisson, VVD, Matip, Adrian, Thiago, Hendo, Millie, Mo and Bobby are our over 30s.
Adrian doesnt play.
Millie will surely be gone in the summer.
Matips contract expires in 18 months odd and I cant see us extending that (maybe even sell him before)
You'd expect Hendo to take on the Millie role and see his minutes reduced
Alisson is a goalkeeper, you might as well take him out of the stats considering most top GKs go at least to their mid 30s still at the top level and often further
VVD again you see CBs going deep into their 30s so having a 31 year old CB is hardly a disaster
Thiago has never been reliant on pace or anything so there's no reason he can't go to the same sort of age as Modric at a similar level
So I'm really not seeing the problem with keeping Bobby, and as ever the calls for him staying...but taking a massive pay cut are just fanciful nonsense. I dont feel particularly strongly about it either way if he stays or goes, but the age of our squad I think actually has very little to do with our problems this season. One of the main issues is that we havent refreshed midfield, and we've kept on carrying Ox and Naby as 'first teamers' when realistically neither one has been for a few years now (consistently). Lose them two in the summer, along with Adrian and Millie, and get a couple of 23 year old CMs in and the 'average age' drops us down to one of the youngest squads in the league. Start adding fanciful signings like Bellingham, and youngsters like Morton, Bajcetic, Gordon, and it gets even younger. So keeping Bobby isn't some major problem. With those four (Millie, Ox, Naby, Adrian) you're also dropping half a million odd a week in wages so again, keeping Bobby for another few years isn't going to stop us making signings elsewhere. He's well on course for his second most productive season here, its not some mental decision to extend his contract.