It is indeed not easy to buy players through negotiations. CPU teams will react the same way as human managers, which means that it is not easy to wiggle their best players from them.
Also keep in mind that CPU teams won't respond to offers when you are in pre-season. This is to prevent that human managers won't have the full starting squad available when they start managing that team.
Sorry about the confusion, but the one with 3 Bosscoins is a visual glitch. 80% of 191 is 38.2, which gets rounded up to 39 Bosscoins. Is this from the iOS or the Android OSM app?
The more expensive players are more difficult to sell. And then there is the randomnes that could either be in your favor or not. Sometimes you sell a couple of players really quickly and other times you will have to wait days before they get sold.
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Transfers are for a large part random, which is not appreciated by everyone. Gamebasics knows things needs to be changed, but it will require a huge undertaking and is therefore considered as a long term project.
Also, on 16 and 17 April we had the Transfer Madness event, which means that selling chance had increased. That way it is a bit easier to sell expensive players. I take it that these screenshots are from those two days.
If there is a human league moderator, that person can kick inactive players once they are inactive for atleast 72 hours. There will be an icon next to their managername on the managerlist.
If you are playing in a league that has 'OSM' as the league moderator, then it is impossible to kick inactive players out of the league.