Thinking about it in terms of the 3-4-3 or 3-5-2 formations that Conte has played:
GK: Lloris keep. Add a new second choice keeper (but one good enough to challenge for first choice). Keep Austin as 3rd choice. Gollini can go.
RWB: Need a new first choice player. It might make sense to loan Royale back to Spain in an attempt to raise his stock a bit again before we sell him at a later date or do another U-turn to a manager with a 4 at the back system. Doherty might be worth retaining as experienced back up just because we otherwise have too many players to buy in one window.
RCB: Romero should establish himself as first choice and is therefore kept. Tanganga doesn't seem good enough on the ball to play as either an RCB or a RB so should probably be sold. Sanchez has had his ups and downs but I think we need to try to bring in better,so he can also be sold. We therefore need another right footed CB option as an alternative option to Romero (which would also allow Romero to provide cover as the middle of the three).
CB: Dier should be kept, he has improved this season under Conte. Rodon, doesn't seem to be trusted and should be sold.
LCB: We need a new first choice player here. Davies should be kept as back-up.
LWB. Both Regulion and Sessegnon should be kept.
CM1. We need a new first choice player I think. Skipp should be kept as back up. Winks can be sold. Impossible what to say about Sarr at the moment but I suspect he should go out on loan.
CM2. We should keep Bentacur as current first choice player. Hojbjerg should be kept as back up. Ndombele can be sold. White can be loaned.
AM. We don't really have a bona-fide attacking midfield player in the squad. Lo Celso is perhaps closest and we should sell him to attempt to bring in a better player more suited to the PL.
RWF. We should keep Kulusevski as current first choice player. We need a player who can challenge him for that position. Moura can probably be sold.
CF. We have Harry Kane as first choice and should keep him. We desperately need a back up to him. Scarlett should be loaned
LWF. We have Son as first choice and should keep him. We have Bergwijn as backup and should probably keep him. Gill might as well be sold back to Spain to raise some precious funds.
Sell/release:
Gollini, Tanganga (sell), Sanchez (sell), Royale (loan), Rodon (sell), Winks (sell), Ndombele (sell), Lo Celso (sell), White (loan), Moura (sell), Gill (sell), Scarlett (loan).
Buys:
GK, RWB, CBx2, CM, AM, RWF, CF
The good news is that we might be able to bring in as much as £150m for that bunch of sells, of course that doesn't work out as £150m of cash due to agents fees and paying remaining instalments of player signing on fees etc but it is still a decent sum of money that could address some of our needs if we use the bosman and 1 year left market well.
Can't see us bringing in anything like 8 players this summer however. In which case we might have to try to muddle through with Moura as our backup RWF and retain Gill and hope that he can do a passable job as an attacking midfield player. The other option is to sign a player who can play as a RWF or a striker, somebody like De Kettelaere for example.
My potential choices for each of those players (for each position I have tried to come up with one freebie, one reasonably priced option and also a likely expensive option for a few positions):
GK
Freebie: Johnstone from WBA - big advantage that he is also an association trained player.
Reasonably priced: Likakovic from Dinamo Zagreb or Oblak who has only a year left on his contract at Atletico Madrid.
Expensive: Martinelli at Aston Villa.
LCB
Freebie: Romagnoli or Zagadou.
Reasonably priced: Lloyd Kelly (if Bournemouth miss out on promotion). Schlotterbeck from Freiburg and Nd!cka at Frankfurt both have only a year left on their contracts.
Expensive: Badiashile from Monaco. Looks an ideal LCB for our system.
RCB/CB
Freebie: Ginter or Luis Felipe
Reasonably priced: Skriniar or Milenkovic (both only have a year left on their contracts)
RWB
Freebie: Mazraoui - a great long term option. Cuadrado a much shorter term option but a good player.
Reasonably priced: Djed Spece - just a year left on his Boro contract, another with association trained advantage. Both Mukiele at RB Leipzig and Celik at Lille have just 1 year left on their deals
CM
Freebie: Brozovic - we should throw a £250k a week offer his way and see his commitment to Inter. Failing that Kamara from Marseille would be a great free transfer and worth a big wage offer.
Reasonably priced: Renato Sanches, just a year left on his deal at Lille. Mahmoud Dahoud who is in same situation at Dortmund.
Expensive - Kalvin Phillips from Leeds. A fantastic centre midfield player who also showed what a fantastic centre back he was against us earlier this season. Alternatively Gravenberch from Ajax (who only has 1 year left on his deal)
AM
Freebie: Eriksen, Lindgard, Isco
Reasonably priced: Tielemens
, Lemar, Aouar and Guedes all have a year left on their contracts.
Expensive: Soler from Valencia, a fantastic player.
RWF
Freebie: Pavon, O Dembele
Reasonably priced: Matteus Pereira - criminal that European teams allowed such a good player to go to Saudi Arabia last summer. De Kettelaere - though probably sits at the very top end of 'reasonably priced'.
Expensive: Raphinha from Leeds is a brilliant player.
CF:
Freebie: Belotti, Dybala, Origi
Reasonably priced: Brereton Diaz - out of contract but Blackburn will be due a development fee. Zapata, M Dembele and Embolo - all only have one year left on their deals.
Expensive: Osimhen from Napoli... Think he'd only be in our price range if we were selling Kane.