Paid about $1000 out of pocket for the windshield, replacement, and recalibration. That was at a local shop (had to order the windshield from the dealership). Safelite was like $1900 out of pocket.
I have a $500 deductible on insurance, but didn't want to have a claim, so I just paid the extra...
I was in the same boat as you are, trying to decide between the lower trims and the Offroad (HALOs weren't out when I had to buy).
What ultimately made me decide to go with the Offroad was the extra off road capability if I needed it and the softer suspension (I don't want a harsh or stiff...