The old shidduch system

We still have parts of that system. Like the traditional Jewish dowry that you speak of, the girl’s father today still usually supports the boy in learning or starting out in marriage or simply setting up the new home. And by some communities in Klal Yisroel today (Chasidim, some Sefardim) the shidduch is more or less arranged, even if it is done at a later age then the tradition you cited.

FSM: +1

Nope.

In the “good old days” most Jews lived in villages (with no more people that the typical shul, and often far fewer), and the nearest village was often hours away. Consider if one had to find a shidduch from a single shtiebel in Brooklyn, and the next shtiebel over was in New Jersey – and cities such as Baltimore and Boston were a week away. The role of the shaddchan was very different back then, and people were probably a lot less fussier. Oh,did I mention than most women died from complications of child birth, and most men (and childless women) rarely survived to middle age, and few children lived long enough to become parents.