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Aftermarket Wheels Disadvantages

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I went with a 20" wheel because they looked better than 19", but didn't have the limited tire selection and cost of 21" ... and I chose Conti Extreme Contact DWS.
I think 19's look a little small, but a lot of my driving is on the crappy, pothole-strewn streets of L.A. so I was apprehensive about the low profile of 21's ... so I went with 20's, which I think are in the sweet spot of not-too-big and not-too-small ... my tires are Michelin Pilot Super Sports, staggered, 255/40 in front and 285/35 in back ... there is a slight rub in front with extreme wheel lock, but only in reverse, and 245/40 would a better fit, but unfortunately the PSS doesn't come in that size ... so I'm curious, what size are your Continentals?
 
offset is what matters there. My 9.5"s wont fit on my fronts

Exactly and to offset the additional 1.5 inches compared to the stock 19x8 you would need to lower the ET to 2. But that would probably put the outer end of the tire outside the fender (if that's the correct word?) which I guess isn't exactly recommended (or legal?).
A 19x8.5 usually have a ET of 32 (like the rial luganos) and fits so maybe you could go with ET7 or something but I still think it will be a problem...
 
I think 19's look a little small, but a lot of my driving is on the crappy, pothole-strewn streets of L.A. so I was apprehensive about the low profile of 21's ... so I went with 20's, which I think are in the sweet spot of not-too-big and not-too-small ... my tires are Michelin Pilot Super Sports, staggered, 255/40 in front and 285/35 in back ... there is a slight rub in front with extreme wheel lock, but only in reverse, and 245/40 would a better fit, but unfortunately the PSS doesn't come in that size ... so I'm curious, what size are your Continentals?
I called to request that Michelin offers a 245/40/20. The Super Sport is the best performing tire on the market and should really be the only option for these highly engineered cars! Pirelli P-Zero is still a good option for now since they come in 245/40/20. The 255/40 is the size that everyone wants because of the sidewall, it's just some cars are slightly rubbing in reverse.

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Also, Model S owners should definitely consider the build quality and safety of a high performance wheel like HRE. You want to make sure the aftermarket wheel setup enhances the driving experience and look of the car.
 
What is the width and offset of the stock 19" wheels? If I wanted aftermarket wheels that fit the same tires, what are the best measurements to look for? Someone told me staggered wheels are when the size of the wheels in the back are bigger, and so you cannot rotate tires. In that case, I would not not want to buy staggered wheels. Also, can someone explain what a concave wheel is and the disadvantages/advantages of a concave wheel?
 
What is the width and offset of the stock 19" wheels? If I wanted aftermarket wheels that fit the same tires, what are the best measurements to look for? Someone told me staggered wheels are when the size of the wheels in the back are bigger, and so you cannot rotate tires. In that case, I would not not want to buy staggered wheels. Also, can someone explain what a concave wheel is and the disadvantages/advantages of a concave wheel?

A concave wheel has the spokes going from near the outside of the rim to the hub giving a bowl like effect, as opposed to going radially to the rim base. It's basically an appearance item. Some examples are here. Other than looks, I don't know of any particular advantages or disadvantages provided the offset and rim width are correct for the car (and the manufacturing quality is good).