How certain are you regarding the need and desire to sell? I can't say I have a detailed understanding of what's going on at Southampton but a lot of the talk in the last 6 months has been fairly negative regarding the ownership and the club's ambition post Cortese. There was reports a month or so back that you'd lost £20m odd and that this shortfall would need to be made up going forward.
Purely from a financial point of view you could afford to hang on to Shaw for another season or two without taking much of a financial hit on any future sale but I get the feeling it's now or never for Lallana if you want a decent fee. Every year he gets older the likelihood of a club offering anything like £20m diminishes. There's not a huge market for him and if he doesn't have a great season again next season I can't see anybody offering a decent fee for him again.
I can understand, with Lallana's age, why we might be prepared to let him go ahead of Shaw. I'd rather keep Lallana, but that's just me. I think it would be more of an acknowledgement that he is further along in his career than Shaw and has given us a fantastic service, so it would be with good wishes that he'd be allowed to leave.
We owe £20m in transfer fees this summer without having bought a player as I understand it. I expect we'll be getting rid of Osvaldo though which will at least get a good chunk of that back.
Since Cortese left, ambition of the owners and new directors etc has been questioned a lot and until we see some positive news on Pochettino's contract, I suspect it will remain. I remain positive that the board do want to try and kick on from what has been achieved this season and there have been a some strong rumours (albeit on a Saints messageboard from ITKs
) that Pochettino is signing a contract with Shaw staying at the club but Lallana being allowed to leave as above.
Southampton, through Cortese, were one of the few clubs that opposed the FFP initiatives. That's because Cortese wanted to throw money at everything to take us to the top. Understandably, the owner wasn't that sure of this and they parted ways. That's not to say though that there is no ambition. If there was no ambition at all and she just wanted to dismantle the club, I doubt a few of the appointments upstairs would have been made that have been.
As you can see, I'm trying to remain positive