Well I began taking apart the car and removing the starter and found that a part of it was bent. I'm not sure if that's the solenoid or what it's called but I'm pretty sure it's the reason the car wouldn't start.
I managed to accidentally break spade connector while testing and decided to replace the start with a brand new Bosch starter and the car started up first try!
There's nothing wrong with aftermarket, so long as it isn't a Chinesium special. I put a reman Bosch starter in mine three years ago, still trucking strong.
Every new starter will be smaller than the Bosch item, they have all gotten much smaller over the years. It will still crank faster than the old Bosch did.
Sounds like you just need a new starter. Best advice I can give you is to buy a new starter from a reputable brand, like Bosch.
So, replaced the starter, and that was that issue.
Just had exactly the same problem on my '09, needs a starter. Well more accurately the solenoid that pushes and pulls the starter teeth onto the flywheel is underperforming, and when cold it doesn't get off the flywheel fast enough to keep from barking the starter motor against the faster spinning flywheel.
I bought a Bosch Reman for about $260 with a 5 year warranty, went in with a moderate amount of persuasion. The oil filter, dipstick, oil pressure sensor have to come out to do it. You being from Chicago might have to fight to get the dipstick holder out without breaking it.
i also noticed that the starter is the original bosch and the positive power lead going to it has some of the insulation cut off right where the wire bends to screw to the starter.
All of a sudden one day I started up my car just like normal, let the glowplugs heat then bump the key just long enough to get it started, but this time and every time after, the starter grinds right as the engine fires and as it disengages the starter makes a grinding sound just like i've held the key too long even though I havent. I took the (2 month old rebuilt bosch) starter off and checked everything and its all clean, I greased everything and re assembled. Still the same. The problem is still present on the old starter, we suspected it to be the sprag clutch at napa.
Volkswagen did something similar with the starters on the 70's/80's Rabbit -- They installed it mere inches from the exhaust, which led to premature solenoid failure. I installed a solenoid bypass button and mounted it under the dash after the 3rd starter replacement in 5 years.
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