I am looking at buying a 1983 Mercedes 300D turbo diesel.
It has 302k on the clock. Runs good..
Known issues are -
Two rust spots, one just under the rear window passenger side, and a small one at the edge of of the rear wheel well on the passenger side.
The passenger window and the rear drivers side are stuck up. seemingly inoperative.
The gent selling wants $1500.
Any known issues I should look for before dropping some dough.. or is this something I should avoid?
I do have experience with euro cars.. previous car was a BMW 325CI.

Pictures -

 

Your ability to afford the Car is really going to depend on if you are able to fix it yourself. This lesson has been learned by myself through my experience of owing one.

At the mileage listed it may be a candidate for a new Timing Chain. The best quality Chain all by itself is in the $115-$150 range. The proper tool to crimp the Master Link to the Cain is around $250 and there are some parts you need. But, with the parts and labor the cost shoots up quickly.
Someone needs to get under the Car and inspect for rust. Take a special look at the Rear Trailing Arms as like on my Car they can be rusted through.
Also under the Car the Rubber Flex Discs and the CV Axle Boots need to be checked for Cracks (the CV Axles are filled with Oil that can leak out if the cracks go through the Boots).
Up front you need to take a look at the Motor and Transmission mounts. If the Motor Mounts collapse it is possible for the Drive Belts to cut through the Oil Cooler Hoses.
Look at both the Oil Cooler Hoses and the Transmission Coolers Hoses. If they are seeping Oil they need changing.
Notice I have mentioned a lot of stuff that is made of Rubber. The Suspension is also mounted on Rubber.
Unless they are really bad you can not see if the Lower Control Arm Bushings are going bad and you may not know until your tires start wearing excessively (it happen to me).
You can see more of the Upper Control Arm Bushings so you may be able to tell if the rubber in them is cracking badly.
If you do work on your front suspension that requires you to compress the front springs (like changing the Lower Control Arm Bushing) you may find as I did that they regular Coil Spring Compressor use on gas Cars is not strong enough.
Even, the cheap copy of the correct Coil Spring Compressor is around $180 on eBay.
In my cast after trying to use the gas Car type Coil Spring Compressor I ended up making one of my own so I could get the job done and not have to pay the $180.
The Front Springs must be at least 3 times stronger than a gas Car Springs are.

It is common for the Rear Window Regulators to get bent in use they are around $225 each now (I had to replace one; I was able to reuse the other by bending it back into shape and reinforcing it).

I am really not trying to be negative but unless happen to get extremely lucky within the next 2 years the car is going to need some work.
My 84 300D (196,000 miles on it when I bought it) had the Suspension Rubber issues, Motor and Transmission mount issues, CV Axle cracking Boot and even some window issues.

A previous owner must have changed the Drive Shaft Flex Discs because they look good and you can see where someone marked the Drive shaft. However, I did have the Cracked rear CV Axle Boot issue.
It would be a lot to expect 20 some year old Rubber parts to still be in good condition.

 

Well lets just say I am very mechanically inclined, a number of years as mil jet elect tech etc

I have always done all my own mechanical work.

I will definitely take a look at the areas you mentioned before dropping cash on this car.

Thanks for the help!

 

Buy mine...it is a "300" with only 26,000 on this engine...

 

A few more shots...

 

I'm sure its a nice car, but I'm looking for something local/stock look. I never did any external mods to my BMW as I have always thought it cheapened the look of the car in most cases. Internals ... well it depends

 

$500 too much for that many miles and rust.