This is what I usually do with Liverpool If I want a save in which I want crazy money 2 seasons in.
1. First Season - Sell Lucas (20 mil), Johnson (15mil), Enrique (10 mil), Skrtel (10 mil) and Borini (10-12mil). Buy Depay, Tielemans, Romero, Gil Romero/Kranevitter, Balanta and Try to get in Ruben Neves and Adama Traore on Loans with option to buy and try for Zaza (If I'm playing 2 strikers). Plus the usual players for the future on installments and performance linked clauses (Ajer, Jovic/Bonazolli, Vallejo)
2. After first season, whichever position I finish in. I sell Lallana, Joe Allen, Lovren, Lambert, Moreno and sell Sturridge also. Now here is how I go about it, I offer these players out for twice their value and then negotiate. Sturridge I have sold for 30 mil (When he has a bang average season) to 70 mil (City/Arsenal anytime he scores over 20 goals). He is very injury prone. I then proceed to buy Clyne, Koscielny (If Arsenal had a poor season)/ Vertonghen, Sule, Aaron Cresswell, Giroud/Llorente and any one out of Aboubakar, Higuain, Barbossa, Berardi). I then try for Ruilli. Another thing, I never used to sell Sterling until he started with this contract fiasco in real life (I'm a Liverpool supporter!), Now I try to get clubs to play **** loads of cash for him or use him as a bargaining chip to get Phil Jones/Ramsey/Wilshere/Shaw. I also make the moves for Ruben Neves and Adama Traore permanent.
I usually have a world class team by season 3 and the board also makes about 70% of transfer revenue available by season 3 and 100% by season 4.
Though I start with first window disabled when I am playing Liverpool ( a serious save when I won't splurge or sell and continue using the present core as my nucleus.)
EDIT- Never and I mean NEVER sell Balotelli. (He is the polar opposite of his real life self in the game)
EDIT 2 - I also forgot to mention that I sell Aspas, Assaidi, Luis Alberto, Coates in the second season. Usually these sales get me 25 mil in the bank too.