2) On a player you may see what he had cost before (and god knows when that had been), but not what was his skills and status, and not what other players with a set of skills like his had been cost.
The current game design choice is to keep all player skills hidden (except when they are actively being sold). Making the skills at transfer time permanently visible would change this choice for a large number of players. This is because many teams buy players whose training is finished (and will never train these players) to complement players who they train themselves. I don't see the BB's changing this design choice easily or abruptly.
3) You will not see current skills, but skills when the deal had been set.
In addition, the naming is irrelevant, so it can be removed from the information the TLH will show.
This is a more interesting possibility. If the names of the players are not shown (and the skills of individual players cannot thus be unmasked), what we could go for is a user-controlled transfer price estimation (TPE). As I think you suggested earlier in the thread, much of the existing code could be used for this feature. The current TPE system looks at some rough model of equal skill set/age/etc. in past transfers and gives the estimated transfer price for each player who is being sold. The weakness of the system is that there may be no useful comparisons available (we get no TPE) or the comparisons are spread across very different price points (which means you need some expert analysis to figure out whether the bottom or the top of the range is more relevant for the player). We do not know the model which was searched for. By allowing some user control (such as the current TL search), we could get more relevant information. To many users it would allow better to understand which price point in the suggested range they really should be looking for.
There are some negatives to this, too. Giving more user control will most benefit those who will take the time to do the analysis and who best know what to look for. These users are not newbies, who would generally perhaps not benefit much if at all. On the other hand, it would be possible to find out the skills of some very special top players by narrowing down the searches. Perhaps this is not a real problem, since many active users/NT staff/etc. check all top players from the TL anyway when they are being sold. Someone having the right contacts can therefore already get the skills of every top player that has recently been listed. The search feature could just help make this information available to a larger group. Okay, so the newbie issue is probably the major negative point.
An added benefit is probably that some active users would be more likely to report overpriced transfers, which could help keep the game fairer to us all.
I anyway think a key point here is that the player skills are meant to be as unknown as possible for other users than the team manager (similarly, NT manager). This is a design choice, which realistically will not be modified in order to make the transfer activity easier.