I installed my Extreme extensions right after I got the car home. I live in NYC and drove through Manhattan many times without issue, but I mostly drive to and from the racetrack, with an occasional event/cruise in between. My front splitter has a few scrapes and the rears are shaved. My car is set up right between the street height and track height. The biggest problem is constantly having to scan the pavement ahead of you, making sure you dont hit a pothole or a dip. Roadkill is an issue too. First the front extension flattens it and then your rear blades slice it up. I wont go into details, but let's just say it's not fun to clean.
Keep in mind that Extreme extensions are useless anywhere but the racerack/autocross, so if you dont track your car, dont bother putting them on unless you want to impress the bros at Cars & Coffee.
Yes, the extensions are a PITA to install, even with the right tools. The issue is mostly with the front since you cannot use any sort of power tools and have to unscrew 14 bolts by hand with a small wrench, replace the extension and screw them back on. You can use a power tool in the rear, but those screws have to be torqued to a spec, which wastes more time. And yes, you have to jack up the rear. If you dont have a jack that's long enough to reach the center jacking point in the rear, you will have to jack up each side individually, install rear extensions there, lower the car, jack up the other side and repeat.
I may be very slow, but it took me just about 1.5 hours to install both the front and rear, including jacking the car up, etc. I recommend you go through a process at least once to get a feel for it, after which you will never want to do it again unless absolutely necessary
If you have your car set to a street height, you will eventually scrub when entering/exiting driveways, parking lots, etc. Just go very slow and you will be OK. Those parts are unpainted plastic and are consumable (although the way Dodge prices them indicates completely the opposite). Don't worry, you are not the only one stressing about these things. I was too. Then I listened to Steve and just started enjoying the car.
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