05 SS Supercharged || 3.8L || 127xxx miles

During the cold months, I get a weird grinding issue. It doesn't always want to start the first go, and tends to grind intermittently. Usually it starts after the second or third go. Today, it almost didn't start. I couldn't pin point anything, and don't have a lift so I've brought it to my families mechanic (who's very trusted) and asked to see if maybe the starter was bad or teeth were missing on the starter or flywheel. Nothing. The more I think about it, I'm wondering if the solenoid on the starter is bad and isn't always pushing the gears together. Ideas?

 

Sounds more like a bad bendix than solenoid.