It really depends on the woman and how important her inheritance/money was. A rich heiress without kids? A great catch (Eleanor of Aquitaine's colorful marital history didn't discourage Henry Plantagenet from marrying her and adding Aquitaine to his empire, and Isabella I of Jerusalem famously remarried while still visibly pregnant with her late husband's kid).
On the other hand, a younger daughter who didn't stand to inherit anything would be a harder sell (although, depending on the terms of the will, she might also have more freedom to pick her own husband if she was financially secure enough).
