How about having negotiation periods? At the end of each season a new deal is negotiated (an increased pay rate is listed) You can either choose to re-sign the staff or look for another option.
Oh, and manager could also improved their skill, of course that would cost money, but it would become more real. But the improvement shall be reaally slow, because a player improves quicker than a manager in real life.
You can do this right now. It's called buying a new staff member -- you pay money, his skill improves.
PlayersI know that wages are related to the skills of the players but what about rounding them. I don't find it so realistic to pay a player $5.472. I could pay him $5.500... This way, in economy we won't have a balance of $538.052 but just $538.000 which is by far more realistic... Also, the TV contracts can be rounded. About Atendance and Merchandise leave them as they are (many fans buy just a pair of socks which cost $5.99 or sumthing)
StaffI agree about staff weekly raises but not that much... I also agree with the staff improvement. You could round staff wages too. e.g. This week's salary $15.000, Next week's salary $15.100