Starter issues on my W116 300SD
 

Okay so I'm having some starter issues. When i turn the key its as if the starter isn't catching or grabbing whatever gear it needs to grab to start cranking the engine. It takes 3 to 4 tries to get it to "grab" whatever it does to get the engine to crank. What is it's problem?

Sounds like your starter is the problem. Earlier this winter when it first started getting cold my starter would spin for a fraction of a second then just "Whhhiirrrrrrr". I replaced the starter with a known working used one. Haven't had a problem since.

I would first check to make sure your starter is solidily in place. It could have jostled loose and is not making good contact.

I'm sure others will chime in with more about specifics about the starter like springs and bendix's, but unless you are rebuilding it yourself it is probably a moot point as you most likely will replace the whole unit.

Good luck.

Could be as simple as old cold grease causing the bendix to stick on the shaft or it could be as serious as damaged teeth on the ring gear of the flywheel. You could pull your starter and fire it up on the bench to see if the bendix is moving smoothly. If not, clean up the shaft, regrease, get it moving smoothly and reinstall. You could probable get a visual on the ring gear by turning the engine by hand and looking thru the starter hole while it is out.