Personally, I feel like I made a huge mistake with the 550. I love the car but wish I had just done the m5.
I went with the 550 to keep a lower profile as I'm currently building a house and for a couple other reasons. I got the mod bug way worse than I intended to and it feels kind of dumb modding a car that isn't the best. i planned on doing wheels and maybe dinan stage 2, then i found this forum... and it was all over. I personally am not a believer in trying to "catch up" with a higher model but that is exactly what I'm ending up doing.
That being said, I do love my 550 and I will enjoy it until I get my M5 when the next model comes out in 5 years or so.
If the money isn't a big deal I'd go m5. If your looking at resale and your car as an investment, you've picked the wrong brand.
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2017 Mclaren 570s
2015 Porsche 911 GTS Manual - Gone
2012 550i M Sport Jet Black - modded - Gone
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