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I would like to thank everyone in advance for your help and suggestions!

I am looking to buy a 97-99 S-500 or possibly a 00 S430. This will be my first MB and the one car I have wanted since I was old enough to know what it was. That said, I like to be as educated as possible before I "jump" into it, especially when it is a car purchase. My questions for you are:

What problem areas should I be concerned about?

When I find one I like, are there any characteristics I should look for that would indicate a possible problem?

What routine maintenance is suggested/needed at what miles?

I have been told before that I need to make sure it blows cold air because the condenser (I think) is known to break down. Being that it is located behind the dash, the dash must be removed for repairs and typically costs $3,000 - $3,500. It is problems like that I would like to be aware so I can be prepared should such a situation arise. Again, thank you so much for your help!
 

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bnzlva
So you favor the 140 chasis than the new 220 S-Class. I know many people whose favorite Benz (if they could buy one) would be one like you are looking to buy.
The 140 chasis S-Classes have common repairs and things to look out for. You are correct in a way to make certain the A/C works good, but the
condenser you mention is in front of the radiator, the evaporator is what is part of the heat box and the dash must be removed to replace the evap.
Just make sure the A/C is operational (hot and cold).
Oil leaks. watch for them, depending on where it is from, could be costly. Common ones I have hear of are Head Gasket, Front Cover on Engine block, Oil level sensor (right side of engine right above oil pan), just to name common ones. If it is bad, you'll notice right away, If it is more of a seep you may have to really look. Other leaks/seeps you should look out for would be from the steering gear box, transmission (not so often, but still look) and Rear Diff.
Check and Inspect the belts, pulleys and hoses.
Steering, if it feels good while driving it, it should be ok. On the test drive listen for clunks when going over large and small bumps (possible ball joints in front or springs), be sure to notice if the steering wheel if off center, be aware that road crown and a drift is different than a pull. If you could, check the steering shock absorber (under vehicle), if it is a 140 it will not have a rack and pinion (hence check steering gear box for leaks.)
Check to see if tires are wearing evenly and if there is any tread left.
To the trunk, be sure you have a spare tire (that is not flat). The battery is on the right side and just by looking at the battery, if it is MB brand or after market, if it is MB good, but look to see if it looks old or new, the new MB batteries have white handles the older ones have black handles, both batteries will be white casing.

I'm not 100% sure on when exact the follow need replaced...i think its
spark plugs 30k miles.
Trans. oil and filter. 30k.
Power Steering fluid and filter (if equip) 30k
fuel filter 15k
coolant and brake flush 2 years
wiper insert 15k
air filter 15k
etc etc...
Will depend on if the car you get has FSS or not, to tell you flex A or B service is due. If the car pre-dates FSS you will have to go by the miles on your odometer. (as above).
Last thing major that I can think of is brakes, check to see if and when they where replaced last and if they where MB brakes.
 

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good call stuart...i must reiterate a few of his points...if you are looking at the 140 car, MAKE SURE THE EVAPORATOR HAS ALREADY BEEN REPLACED. this is a big expensive job and will need to be done over the life of the car. the steering gear will leak eventually, although most times a reseal job will make it good as new. the diffs leak (as most do), and it is not uncommon to see broken springs on the vehicle. the bottom part of the coils can actually break off. lower control arm bushings are another common repair. these cars can be expensive to maintain due to the cost of parts (as one would expect with a car that originally retailed for nearly 100k). extended warranties are not a bad idea. there are some truly pristine 140's rolling around, the 99's of course being the last and best example. if you decide to go with the 220 car, check the repair history of the airmatic struts. there is a relay that can stick and burn out the pump causing the struts to collapse. this in turn tears the bladders inside. oftentimes 220's will come in sitting way too low and we will have to replave all four struts, the pump and the relay. the struts also seem to like to stick to the front spring links, so these are often replaced with them. this adds up to a very costly repair. the 220's have been pretty reliable for us, but again, parts are very expensive. i hope you find a great example to drive. it is impossible to find a more comfortable, balanced vehicle on the road.
 
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