A few minor suggestions, not vital but would make things more realistic.
Players have medicals, then your Fitness Coach/Ass Man would give you a report and/or view on his fitness, injury pronenes etc.
When a player signs, when there should be some sort of media involvement, maybe a question to the manager asking why you bought him etc. I think a player stating his detemination or hoping to learn from player are examples of this but there could be more options, like they were swayed by the manager or other player giving advice.
Some more "clauses" in the contracts. I.e some players have a clause that if a top 4 club (maybe hard to implement this) comes in, he is allowed to talk to the club.
I think the Friendly tour option should include you taking a certian squad, similar to the international squad being named.
Setting player targets for the season is something i like the idea of. I.e At the start of the season tell "Striker A" you like x amount of goals for the season. Maybe a reward in the conract or just a target so you could rate his seasonal performance.
Being able to visit or read some sort of Fan Club reaction or something, to give a different sides of things that the media would say.