One easy fix would be get rid of Free Agents....adding more players to the pool when there are fewer teams just kills the market
Well, I may be wrong yet again, but I believe that was the goal of adding FAs. If the econ stagnates as previously stated, then I suppose the devs are ok with where we're currently at.
It is a bit of luck. Whether you could 'forsee' the drop in market values coming or not, it still comes down to the timing of the drop and when you choose to make your move. Other than the devs, I doubt anyone can exactly conclude when the deflation would occur, so how long does one wait to make said move? I don't really complain about the market itself, as long as it's equal for all. If we're all playing by the same rules and parameters, there's really nothing to complain about. The thing I do complain about are salaries, but whatever.
I certainly took a rather large hit because of the market, but I do believe I rolled with it fairly well considering I absolutely could not wait any longer to change. Good luck with your transformation.