Your blogger will go out on a limb and presume that these photos were taken in southern California in 1939. The car has a license plate and aftermarket “flipper” hubcaps so it isn’t brand new from the dealer in these shots but I’d like to believe that the photos were taken within a few weeks of taking delivery. Owning a convertible Mercury was a pretty spiffy way for a young man to show the world that he was doing well. Did he also own the boarding house or was he renting a room there so he could afford the car? We’ll probably never know.
Image: orginal source not available, see link info below
“Six years after Prohibition ended in 1933, the Women’s Christian Temperance Union were still holding firm to their ideal that, as it says on their billboard, “Prohibition: the Best Method Against Liquor Traffic” that stood atop their building at Broadway and Temple St in downtown L.A.”
The Railroad Boosters (now Pacific Railroad Society) were southern California railfans who sometimes chartered trips on trolleys and trains. The video at the link is from a 1939 trip they took from Los Angeles to points north of San Bernardino on the Pacific Electric red cars. At 5:32 you can see where tank cars were filled with Arrowhead water near the famous Arrowhead Hotel.
This is a silent amateur movie that offers a glimpse into the greater L.A. area. A few seconds are blank (6:10 to 6:20) followed by seemingly random shots of trolleys that may or may not have been part of this trip. In the comments section of the youtube link there are some mentions of locations seen.