If this is the current case, I would ask for the guy that they will be letting go's quote straight up. It will save you much time and figuring if it is a low ball contractor. If it is in your ball park figures on what you can do it for, then crunch numbers after you see it. If it is stupid low, respond to them that you are going to be minimum double or triple his number and ask if they still want you to proceed. Not worth wasting your time on work that is unobtainable.
Culdesacs are a pain, but with a properly set up pickup, you can fly threw them. When I did culdesacs, we had rally routes of 20-30 culdesacs per route. They were 4-5 hour routes for one truck. 10-15 minutes in a little culdesac feels like and eternity when you are in the truck.
Roads go quick. Typical rally roads with pickups were 4 passes w/ curbs. 4 passes was only due to the fact that if they were on a rally route, they were a dead end (or the city trucks would have done it) so you had to make one more pass back out or it was 3 if not a dead end. Non curbed were 3 pass unless deep enough snow that you had to "wing" in case it froze.