I think a bunch of it depends on how much room and where you park them. Two car driveway and multiple cars on the lawn or parked in front of neighbors' houses = too many cars. If you have enough garage space and driveway spots, or a good sized plot of land, then that isn't much of an issue. Then I'd say that it also depends if you have depreciating cars that you aren't driving much. Lastly, insurance costs. I'm on the verge of too many cars, but they aren't costing me anything. 8 cars, three garaged and the driveway fits 4 easy, 5 in a pinch. When I finish getting the side yard paved, plenty more room.
2024 Chevy Malibu company car. Effectively better than free (they pay all of the gas, maint. insurance, etc, I pay $200 per month and get taxed on personal use.
2019 Ford Expedition- wife's daily driver
2004 Nissan Titan - Bought new, bought back from insurance when rear ended and totaled years ago. Cheap work truck and tow pig.
1995 Miata M. Need paint, top, and interior.
2005 Subaru Legacy GT Wagon manual. Excellent condition, pretty much like new. Partly because it's been in the garage for years waiting for me to install a new engine that I built for it. It's taken a back burner, like the Miata, due to all of the house projects.
1992 Mitsubishi Galant VR4. Car was pretty much done, needs a headliner and the clearcoat is peeling. Did an oil change and found glitter in the drain pan. Hopefully just a balance shaft bearing- no glitter in the oil filter- but it's going to have to wait until after the Miata and Subaru are done.
Just added this month. I have a 16 and 17 year olds that are working on their licenses. Their older cousins just bought new cars and sold them their old ones for $500 each, a 2012 Chevy Cruse and a 2013 Chevy Malibu, both in good condition. Didn't need two more cars to park, but can't pass up any car in good shape for $500. Plus should be cheaper to insure with their own cars, and I no longer need to consider letting them use the Subaru- it's too nice of a car for a teen, not to mention way faster than a first car should be.