Always ask on the ferry, it's likely you can find a car going for a very long journey. I got lucky and found a car going directly to Munich. Our ferry was going from Bastia to Livorno.

Cars can see you from distance and there is enough space for them to stop. But the problem is, that you are still quite in the center and with sign to Livorno its a bit strange. One car offered me Empoli and second Lucca but I declined both (should have taken Empoli).

Not a frequented gas station. Maybe 1 car left every 5 minutes (cca 6 cars in 30 minutes). One older lady offered me a ride to Viareggio but I declined because I wanted to Livorno.

You're standing a good bit before the sign saying 'No Autostop', and there's plenty stopping space. Tried for a few minutes going towards Livorno without luck (but someone going to Southern Italy stopped) and then due to nightfall arising hitched into Grosseto which only took about three minutes.