Tesla in my area doesn't do the window replacements (use to I understand) and you'll end up using a glass shop but I'd call Tesla and see if they will give you the names of a few places to call that they've worked with. Most of these glass guys will come out to wherever you need them; and due to the cameras most new cars will have in their windshield area, yes, calibration will need to be done afterwards. If your service center where the calibration would be done has a large enough parking lot (or maybe there's a convenient parking lot close to the SC), you might consider meeting the glass guys there and then just a quick drive to the SC for the calibration (inquire about appointment time). Depending on how bad the crack is, you may not have a choice in whether the car can be driven. Be careful in this weather blasting hot air on the windshield as the temp difference could cause the crack to lengthen.
The windshield will come from Tesla to the glass shop, and so if they don't stock them it might be a wait. I'd call Tesla first, get the name of local shops, talk to them about timing and then see how your insurance company handles it--reimbursement or direct bill to them.
