Raise it during the quote every time, because a crew that discovers it on the morning will either charge for a shuttle on the spot or burn an hour working out logistics while the clock runs. Send photos of the street and the driveway turn along with your inventory. A company that works the area regularly will already know half those streets by name. I hired movers in Newton, MA and they scouted the approach beforehand, then split the load onto a smaller truck for the last leg. Mention any low branches too. A box truck is considerably taller than most people assume when they look up. Check whether the town needs a permit for a truck on the street as well, some of the villages do.