Thus far, we have seen how it is forbidden to pressure one's fellow Jew into selling, renting or giving him an item. However, not every attempt to acquire a possession that is not for sale violates the prohibition of loh tachmod.
One is permitted to ask the owner, if he would consider selling the item. This is because asking the owner if he is interested in such a fashion is not considered pressuring him. However, if the owner refuses, he is not permitted to continue asking him to sell the item. Statements such as, 'please reconsider', 'we need it so badly' and so on, in such a setting, are forbidden.
If the owner showed no interest in selling, is one allowed to come back to him with a bigger offer? There is a difference of opinion amongst the authorities on this issue. There are those that say this is permitted. This is because the prohibition of loh tachmod involves embarrassing or pressuring the owner to sell the item when he has no desire to do so. However, many items are not for sale at a certain price, but were the owner to be offered a higher price, then the item would be for sale at that price. Therefore, the owner is not selling the item at this price because he is pressured, rather because he genuinely desires to sell it at this price.
Other authorities are stricter in this question - Rabbi Yosef Shalom Elyashiv shlita rules that it is forbidden to return to the owner with a bigger offer once he has refused the first offer. However, if the owner had given some indication that he would consider selling the item at a higher price, or some change in the owner's situation indicates that he would reconsider, he may be approached again.
One is permitted to try to demonstrate to the owner why it is in his best interest to sell, provided that it would genuinely be in the owner's best interest. A distinguished person may not ask someone for an item even once, if he feels it is possible that the owner will feel pressured to refuse his request.