I've got a problem with my 87 300E.
The car starts, but I have to sometimes crank it twice.
what kind of things can i check?

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87' 300E champagne - Euro headlights and corners, 8-hole rims, 140,000miles/220,00km.

This might be a bit extreme, but I am suggesting to you what my mechanic suggested to me. It might need the valve seals replaced. My problem happens especially when it's cold. It will usually not start the first try. But when I try it the second time, it starts right up. Maybe a little helpful?

Take care,
Michael.

Lower chamber pressure/differential pressure and EHA current come to mind.

Cranking voltage, available voltage and sparkplug condition are others.

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Steve Brotherton
Continental Imports
Gainesville FL
Bosch Master, ASE Master, L1
33 years MB technician

http://www.peachparts.com/shopforum/showthread.php?threadid=37239

You mat want to have a look on this thread for some solutions to your problem.
But, it could be something else
JackD