You can probably lose one.
When the wife and I left the Bay Area for the midwest we kept only one car. It simplified moving and if we needed another we could get one in the midwest.
Soon we'll have been a single-car family for two years.
Old cars are a Prius for interstate trips, and an early 2000s Outback for camping/interstate trips where we need to bring more things with. Prius got severely damaged in our parking lot and I used the insurance payout to help with a down payment on a Crosstrek, which will eventually replace the Outback as well.
I feel bad for taking up the (free) parking space, but the cost of ownership of the Outback when infrequently used is something like a $40 insurance premium every six months. That's another benefit of not driving much -- low mileage and safe driver insurance discounts.
And though insurance is officially "tied to the car" it's really tied to the driver; you can't drive more than one car at a time anyway so the third, fourth, tenth vehicle adds less and less.