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I think the economics are rock solid if you buy an older car with a solid following and lots of data points for market value. I went through a similar calculation to your friend (albeit with smaller numbers) when I bought my 914. Here was my logic:
I needed to have a car that was fun to drive, because life is short and I spend lots of time in cars. So you have 2 options: combine your fun car and daily into one car, or get 2 cars -- a practical daily and a fun "weekend" car (I drive mine during the week too).
Combining your fun car and daily driver for me basically meant buying a BMW -- it's the only car that offers 3 pedals, enthusiast performance, and practicality (try getting an audi with a clutch these days). Getting one with all the goodies, if you get a good deal on a CPO one, means you're into it for $50k...plus insurance etc. And, you've got the "BMW tax" for parts when it's time to maintain it.
If you split them up you have lots more options. At the time I bought a 2-year old honda accord 5-speed for 12k and my teener for $8k. As a bonus...the accord was pre-depreciated, so when I sold it I actually got back what I paid for it (!!!), and the teener I actually sold for a few bucks more when that time came. That BMW, when it came time to sell it, might have been worth half of what I paid.
So that's a $55k differential...$30k in purchase + $25k in resale...not factoring in insurance, parts, etc, which would likely have been more for the BMW than the accord (basically 0) + the teener (~ $1k/yr). That's a no-brainer.
As a bonus, I got to work on the teener which I enjoyed as much or more than driving it, and the savings over the BMW route made it very easy to justify buying the best parts and tools, seeing as how I would never get anywhere close to the BMW cost.
As long as you buy smart and maintain it properly, buying an old sports car of any make / model can be "free" in the sense that it's very possible to get back what you paid for it, +/- 10%, if that ever becomes necessary. So, if you're committed to having a fun car, the economics of buying 2 cars are rock solid IMO.
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