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
WOW, really good points. But it hurts to a III division team to have a manager 5 or 6.