1 Yes

2 Technically no, but unlikely. If your bid is last one on the round, and nobody bid in the next round, you win.

3 No, but if other manager bid on the next round you will lose because you did not bid on that round.

4 They try to scare people off, or have no idea how the bidding system work but just using their instincts instead of trying to understand it.

5 Perhaps they have limited the budget of bidding to 2~3 tokens. More bids increases the money cost of the player which can also make the bidding unattractive to continue.