Hello all,
The GOOD:
About 8 months ago I picked up an 87 E300 for a price I couldn't turn down. It's been my daily driver for 14k miles and is in overall pretty good condition.
The car has 220K on the clock.

The BAD:
It's got an external head gasket leak - losing enough coolant (pure water) that My low coolant light comes on about every 100 miles. You can see it running down the block behind the exhaust manifold.

The trans slips a little when first starting. Once RPM's are up it seems to do ok.

I'm at a point where i need to go buy a Civic as a daily driver, or considering sinking some real money into a $500 Benz. I'm on the fence because i'v heard the head gasket alone could put me back over a thousand bucks (2x my investment at this point)

Any advice would be greatly appreciated.

On a side note - I don't believe there there is a car being manufactured today that is worth buying. I would hate to buy a Civic, but i'm pretty sure it would run for years with no major issues.