The C90 has a pretty high compression ratio for a big twin (8.5:1). The starter is not strong enough to overcome the compression in the cylinders. So C90;s have a solenoid activated compression release on each cylinder that activates when you press the starter button. The front cylinder release is directly attached to the solenoid. The rear cylinder release is opened by a cable from the front cylinder release. Over time the cable stretches and the rear cylinder release is no longer opening enough to relieve enough pressure for the starter to turn the engine. So if you try to start when the rear piston is starting up on its compression stroke it will stop and the engine doesn't turn over, though it sounds like it's trying. That's why it doesn't seem to follow a pattern; it is dependent on where the rear piston is when you try to start it. Putting it in gear and rocking it backwards may move the piston enough to start, but the fix is to adjust the cable so the rear compression release functions correctly. I have over 90K miles on my 2005 and have done it twice; at about 18,000 miles and again at about 75,000.
It requires removing the center chrome piece, both top covers, and the airbox but is otherwise a simple cable adjustment. There is also an adjustment on the solenoid attachment to the front release you should check while you're there.
Try putting the bike in gear when this happens and rock it until you reposition the pistons, then hit your starter and see what happens. ( If you are up against the compression stroke, then you wait a few seconds it gives it time to bleed down the compression.)
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Based on this, do you think it is the decomp that needs to be adjusted???
I have the same issue with my bike. I can tell you that rocking it back and forth does not help. I've had 3 guys push it and then release the clutch and still nothing. I wish you could get at a plug to release some compression.
I didn't realize there was a decomp adjustment. That's interesting and certainly worth looking into. The shop where I've taken it to has no clue and certainly did not mention a decomp adjustment.
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