This is my current thinking (but I am no where near an expert and I am not claiming this is right). This is assuming Conte stays in charge and I'm allowed to spend 50-100m + sales. I would try and fill a squad of 25 like this (all ages are as of 1st Sept 2022):
GK Lloris, Hugo (35)
GK
New GK
GK Austin/Whiteman (23, HG)
CB Dier (28)
CB Romero (24)
CB
New star CB
CB Davies, Ben (29, HG*)
CB Rodon (24, HG*)
CB Tanganga (23, HG)
LB
New LB / Reguilon (25)
LB Sessegnon (22, HG)
RB
New star RB
RB Doherty (30, HG*)
CM
New star CM
CM Skipp (21, HG)
CM Bentancur (25)
CM Højbjerg (27)
CM
Matar Sarr, Pape (19, U21) / New CM
AM
New AM/LW/RW
AM/LW Son (30)
AM/LW Gil (21)
AM/RW Kulusevski (22)
AM/RW Bergwijn (24)
CF Kane (29, HG)
CF
New CF
Loan Out: Emerson, Royal (23)
Release from loan: Gollini (27)
Sell if possible
CB Carter-Vickers (24)
CB Sanchez, (26)
CM Ndombele (25)
CM Lo Celso (26)
CM Winks (26, HG)
AM/RW Moura (30)
Others
CM White, Harvey (20, HG) - Loan, development or squad
AM Alfie Devine (18, HG) - Loan, development or squad
CF Scarlett, Dane (18, HG) - Loan, development or squad
RW Clarke, Jack (21, HG) - Sell, loan, development or squad
GK Austin/Whiteman (23, HG) - Sell or loan the one not in the squad
Why?
- New CF is obvious.
- As I wouldn't keep Gollini, a younger strong backup keeper who can look to challenge Lloris would be very welcome. A homegrown Austin/Whiteman is perfectly ok for me as a 3rd choice.
- Why loan out Emerson? If we can get our money back then I'm happy to sell but I doubt we'd get close. But at 21 he's young and I'm hoping that his troubles are potentially part moving to a new country and part playing RWB. A loan at a club who plays to his strengths might raise his value (look at Gil). Plus, if Conte decided to leave and we got in a manger who doesn't play wing backs, an improved older Emerson could be useful.
- Without Emerson and as Tanganga can't play RWB, we have a space there and getting a New star RB would greatly improve our team. Doherty would be ok as a backup and is PL HG.
- CB: Homegrown considerations means that I'm happy for Tanganga and Rodon to be 5th/6th choice CBs. But I would like an improvement on Davies at LCB, ideally a player who is strong in the air. This leaves out Sanchez who I hope we can get a bit of value from (but no where near what we paid for him). I don't know too much about Carter-Vickers but I doubt he's at the level we want to go to even if it sounds like he's done well at Celtic.
- CM: is one of our weakest areas imo. Getting a New star CM would massively help us. This means getting rid of Ndombele and Lo Celso after their loans finish (at all costs) and getting rid of Winks (who get too much abuse imo). Losing a HG player is not ideal but it's best for all concerned as Winks is clearly 4th choice atm and new signings would relegate him further.
- I don't feel we hare strong enough with our options in attack so I would like us to get a new AM/LW/RW who can open up stubborn defences. I'm hoping Bryan Gil will be ready to play in England after a full pre-season with Conte. If he's not then loaning him (or even selling if we make a good profit) would be ok, I just wouldn't sell Moura. At 30 and not being in the first team, it's a decent time to sell Moura but he's perfectly fine as a squad option.
- Of the two in purple, to keep with my rule of a maximum of 7 signings, I can only do one of these.
- If Pape Matar Sarr is ready to be part of the squad or wouldn't benefit more from a loan, then I would keep him as a CM option and hope he can have an impact like Skip (I don't know much about Sarr apart from he was highly rated).
- On the other hand Reguilon is someone who I really liked when he first joined but since he's had Covid he's been a little hit and miss. But I'm not sure if I had new signing bias at first or if I've got disappointed bias recently. I still have hope that there is a player in there that just needs to fully recover from long Covid (if he has that).
- Sessegnon does seem to be improving, is still only 22 (in the summer) and has the huge advantage of being homegrown - although his injury record is concerning
- If Sarr is ready and Reguilon can become a top 4 LB then I'd keep them both (maybe get another RB). If neither of them can do this then I would keep Reguilon and get in another CM as I think that's more pressing. If one of them can't do the above then I would look to loan (Sarr) or sell (Reguilon) and get a CM or LB in.
- Homegrown- this squad meets the PL HG rules with 8 players. If we don't sign any HG players, we would only have 5 HG players to use in Europe with Davies, Rodon and Doherty not counting towards that.
- If this happened, I would not include 2/3 key players (2 if Sarr is in the squad as I think he gets a pass for being under 21) in the squad for Europe if we are in the Europa or conference league. Depending how the season goes before January, I would reconsider this at that point.
- If we somehow get into the top 4 (I would be shocked) then I would not include 2/3 fringe players - although I'd make a bigger push to try and make sure some of the players we're bringing in are European HG
I don't really know about what the players that we should sign for these positions, I don't know enough about football outside Spurs tbh.
I'm not claiming that this is right btw, I'm nowhere near knowledgeable about football as I would need to be. So feel free to tell me where you think I'm wrong and what you would do.