I'm a life-long car guy as well. I road-raced with SCCA and NASA for 5 or 6 seasons, and although it was "on the cheap," it wasn't really cheap. A weekend cost me about $850 to $1,000, if memory serves me, much of it was tires. At age 49, I got DQ'd for some BS and hung up the helmet. It was the best thing that could have happened to me, as it cut the ties to the money-draining activity. As the saying goes, racing is an illness, and the only cure for it is poverty.
My business partner did land speed racing between 1991 and 2017. He spent about $80K per year on this hobby (14 land speed records), and that was "cheap" as well, as crazy as it may sound.
I still have (1) my wife's 2002 MINI Cooper that we bought 10 years ago, (2) our "family car," a 2012 Dodge Avenger that I bought 3 years ago for $4,500, (3) my 1992 Dodge Ram pickup, that I bought 18 years ago for $5,500, and (4) my daily driver, a 1962 Volvo, that I bought 20 years ago for $1,000 and consequently "restored" to driver quality. I also have a 2006 Ducati that I bought 2 years ago for $2,500, and a 1960 Lambretta motorscooter that I bought many years ago. I had more vehicles, but I sold the rest, not to be replaced.
While that sounds excessive, and it perhaps still is, the numbers are not that bad.
(1) MINI.
Bought it 10 years ago for $10K. Has 78K miles on the clock and is still in near new condition. No repairs worth mentioning. Will keep that another 8 years, 'til retirement, then sell it for $3K. So depreciation $7K in 20 years, or $350 per year, on average. That's less than a dollar per day.
(2) AVENGER.
Bought that from the insurance payout of my 1995 Diesel Mercedes that got hit by a truck while parked. Didn't pay a penny extra. Plan on keeping this another 5 years, is my guess, then sell it for $1,500. That's $3K depreciation in 7 years, or $428 per year, or $1.19 per day.
(3) RAM
Bought it 18 years ago for $5,500. Will keep it another 8 years 'til retirement. Will sell it then for about $8,500. Driven 28 years, and then made money when selling. And that's in addition to the money it saved me while working on the house. It has hauled siding, dirt, you name it! A total no-brainer!
(4) VOLVO
Bought that 18 years ago for $1,000. Will drive it another 8 years, 'til retirement, then sell it for $10K. Do the math.
(5) DUCATI
Bought that 2 years ago for $2,500. Don't really have time to ride it much. But if I were to sell it tomorrow, or next year, I'll get all of my money back. Free motorcycle fun!
(6) LAMBRETTA
Bought that 5 years ago for $3,750. Will keep it another 8 years, then sell it for $7K or $8K. Like the Volvo it's on collector car insurance, for $32 annually!
So here I am, still with 6 motor vehicles, and they all together cost me less than somebody's soulless soap box. And the satisfaction I derive from this is priceless!