[drew4392]

I'm on my 5th car within this tier-- Several 335/340/S4s, ... love them all. But, I would like a change.

I've always leased. For me, it has made more sense. It's a nice business write-off, affords me flexibility because I usually don't keep a car longer than a couple of years, etc.

Lately, I've been really itching for the next higher class of car: C63, M3, ATS-V, Quadrifoglio, older 911 or newer-ish Cayman, etc.

The only reasonable financial way I can pull it off is by buying a used version of one of these cars. Typical 60 month financing and very minimal down would result in a payment that I can afford. About the same or a tad more than the typical lease payments of my last several cars. I would be buying with a warranty (Fidelity Platinum, which I've heard great things about) to cover me for 2-4 years.

Here is my concern/question:

Does it simply boil down to, you have to pay to play? I'm worried about being significantly upside down in 2-4 years, or whenever I want to sell. Will the market value stay commensurate with my principle balance? That's the magic question. If I end up having to eat several thousand dollars when I decide to sell, if I annualize that negative equity, then that's the extra cash I would need to foot a lease on a NEW version of one of these cars. Hoping that makes sense?

Thanks in advance for your thoughts!!