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Hi Drew,
You are correct, the transmission is set to start in 2nd gear, so only shifting twice is normal. As far as the rough reverse/drive engage goes, maybe check the fluid level? my own 300e was never exactly "smooth" when it engaged reverse/drive, there was always a solid clunk but nothing alarmingly jarring. And it was the same before and after it was rebuilt.
Overheat problem: check the fan clutch. they are a common high mileage failure point. procedure to check it is (someone double check me) get the car up to operating temperature for a while, shut it off and let it sit for maybe 5 min, open the hood and spin the fan with your hand. if it spins freely, the clutch is shot. if it does not spin freely, then it is good. I think you can also try this procedure when the car is cold, in the morning. Other overheat causes could be thermostat, worn out water pump, somewhat plugged radiator, or the auxiliary fan not coming on when the coolant temp reaches 105C.
Oil pressure guage: the oil pressure sender, located under the oil filter is a common failure from what I've heard, although I dont know if it would make the guage stick on 3. There could also be a broken wire or something or even the guage itself is broken. good used instrument clusters are pretty cheap on ebay if you want to try swapping in a different one..
Speedo cable: it broke? i guess that means you dont know how fast you are going? might want to fix that...i dont think they're too expensive.
Brake pedal: check the vacuum line that goes from the intake manifold to the booster and make sure the connections are tight and that the line is not cracked or anything. The booster itself could be shot, too, I guess.
SRS: I have no idea. Sorry!
Tune up: please make sure to use only OEM ignition parts (Bosch/Beru). I personally only use bosch parts including the hard-to-find H9DC0 plugs, available thru peach parts!. Note: a rough idle on these cars can also be caused by a dirty/lazy idle control valve, and the hoses that go to and from this valve are a common failure point as they dry out and crack, causing vacuum leaks at idle.
i hope this helps! please note that I am not a professional technician, i am going off of my own experiences owning my 300e for 10 years, and doing tons of research about it reading the manuals and the posts on this forum. There are many helpful people on this forum who will be happy to give their opinions as well. Welcome to the mercedes world! The 300e is an excellent car that will give you many happy miles, as long as you give it the care and feeding it needs.
-Chris
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Streetside: 1987 Mercedes 300E Petrol Blue/Green
2014 Ford Mustang Grabber Blue
1999 Ford Ranger Green
Dockside: 1968 Eltro 17
1985 Silverton 34C
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