Got through my first season with Chelsea last night. It was the winter update, so I only had the transfer ban until December and effectively removed it as an issue by setting the game to no transfers in the first window. The season started off with ups and downs, although I picked up a few injuries to add to the existing long-term ones CHO, RLC, and MVG all had. Ended up having to start Batshuayi for the first few games of the season because Tammy Abraham was one of the casualties. He did a decent job but it was Pedro who really carried the team until Abraham was fit again by October. His performances really started dropping off as the season progressed, however, basically starting when CHO was match fit and only declining further from there. Abraham was still top goalscorer of the season, with 16 goals, despite only being first-choice forward from October till February, enough to make him want his wages doubled for just an extra year added onto his already long contract. I managed to talk him down but my new Director of Football later gave one to him anyway. I did manage to talk Jorginho and Zouma down from contract discussions just by telling them how important I thought they were, however. Rudiger has also piped up about his contract recently and doesn't seem as inclined to drop the subject, so he may be on his way out during the summer.
Lost the Super Cup against Liverpool and scraped through the League Cup third round against Middlesbrough but the league was going well until December. I went from competing with Everton for 2nd place to both Manchester teams leapfrogging us and a three team scramble for 4th place with Wolves joining in. Leicester, Arsenal, and Spurs played really poorly and were roughly in that order. My end of season highlight was actually a 5-0 win against Tottenham, who sacked Mourinho and replaced him with Rafael Benitez before Xmas. Watford, Newcastle, and Aston Villa were the relegated but that didn't stop Newcastle from beating us 2-0 on the final day of the season. We could've grabbed 2nd if we'd won and Man City had lost to West Ham, but I wasn't expecting that to happened and they ended up winning anyway.
In January I brought in Alphonso Davies and Vinicius Junior for £17m each, plus Erling Haaland from Dortmund for £65m. Giroud, Willian, and Zappacosta left for Dynamo Kiev, Man Utd, and Guangzhou, respectively, whilst Emerson went on loan to Spurs and ended up playing really well for them. Man City knocked us out in the League Cup semis and we got trounced 4-0 on aggregate by Barcelona in the Champions League round of 16, but made up for it by finishing 3rd in the league, behind Liverpool and Man City, as well as a comfortable 2-0 win over Liverpool to win the FA Cup. We ended up with the least goals conceded in the league (20) and the 2nd best goal difference behind Liverpool. I also got hefty bonuses from both Madrid teams because Real won La Liga and Atletico won the Champions League, thanks to the Eden Hazard and Diego Costa deals.
Currently trying to decide whether I want to run with Jamal Blackman as my backup keeper for the 20/21 season, since Caballero's gone, bring in a different veteran as backup, or even try for Donnarumma since he wants to leave AC Milan. Pedro and MVG are gone too but I'm comfortable with the amount of depth I have in their positions. As I mentioned in the first paragraph, Rudiger is unlikely to stick around if he continues kicking off about his contract. He was probably 4th choice centre back in the season just gone so I won't miss him if he does leave. Alonso is also likely to get the boot as Davies and Emerson can rotate as starters once the latter returns from Spurs, with Azpi providing cover. PSG are after Jorginho, Arsenal want Zouma, and Man Utd seem interested in Barkley, which I'll only be keen on if they make good offers, like £80m+, ~£50m, and £~35m, respectively, and I can get a good future prospects to replace them in the squad. My DoF failed to negotiate transfers/contracts for Sandro Tonali and Federico Chiesa so I might have to stop him from ruining transfer prospects moving forwards. It's really weird understanding the inflated economy compared to FM12; I'm used to £30m transfer fees and £120k weekly wages being the absolute high end of the market. On this game it feels like that's the cost of a decent rotation/backup player.