What if you stop training that player from now until the end of the season? What if you give him single position training in his most salary affected skill?
I had two suggestions there:
1- a snapshot in time, which gave an estimate of where his salary was heading, given his current skillset. It could be a range if there is uncertainty about where salaries are headed, I don't really care. But if you give the player more training, then there are no guarantees.
2- an estimate that updates every Friday, after training.
I think either of those addresses your concerns.
I do not think that uncertainty in this situation is good. Some people might get into a panic about their salaries next season, dumping players, allowing others to cash in. Or we will have a massive dump at the beginning of next season as people are surprised with their new salary levels.
Some of the newbies I have been helping also sometimes get excited about players towards the end of the season, because they have low salaries but high skills, not realizing their salary will increase at the start of the new season. So a salary estimator would also eliminate some of that confusion.
If you have high salary players, assume a 12.5% salary increase. If you mid salary player, assume a 4-6% increase. If you have low salary players, assume nothing.
As BB-Charles mentioned, your definition of high salary and my definition could be completely different. So right now all I can do is assume an upper bound of 10-15% and hope for the best next season.
Run of the Mill Canadian Manager