I think you are being quite harsh -- the transfer market to me is one of the most challenging parts of the game because it is such a mixture of sharks, sheep, pigs and dopes, with a gazillion variables (all the skills, age, potential, and so on). Figuring out a fair price in that world is, I find, very difficult. Through a mixture of other bidders, some who have deep pockets or experience or both, others who are idiots, and you have a very complex world.
To focus on but one variable: I can not figure out the consequences of a "starting price". If set high, say for your player, you put a price of 5 million -- then how many potential buyers have you lost because of the nature of the search engine? If you set the opening price low, say 2 million, you are right, you have a chance that no one bids and the guy goes for under 3 million.
I'm still at a level where my players have many fewer zeros in their value, but the problem is the same. To effectively search for players, to set minimums and maximums in certain skills and salary has made me think through this game much more carefully.
What I have learned is to have as little to do with the TPE as I can get away with! More cheerfully, I have gotten much better prices when selling than when buying.