For almost the first year I lived there I paid rent in person by cheque to a management company office. It was a midtown manhatten apartment in a nice ish building less than a decade ago. They also forgot to cash the bankers draft I had written up for my deposit (five fucking figures that they just didn't notice for years). Real Estate has a surprising number of absolute clowns still for some reason. I guess because it's been easy money for asset owners so they chaff wasn't being squeezed out.