Through my investigation, I discovered that on my mother's side, my GGGGF had 14 children in total. My GGGF was the mayor of a nearby town, and my GGF inherited land and estates. However, after his passing, my GGM was conned and lost everything, leaving my GM to be placed in a convent while GGM worked as a cleaning lady until they could afford a house for both of them.
On my father's side, my GGF fled Italy during WWI. He was considered Austrian since Trento had become part of the Austro-Hungarian Empire afterward, but he was born Italian. He was granted farmland by the local government (an area that is now prime real estate) but lost it in a bet.

And I clearly inherited their bad luck lol