The weather where I have been street-camping has been unusually warm and pleasant with the low in the 30s and the high in the 60s (0-20c); and the last 2 winters have also been warm and pleasant here, so I am considering just staying where I am for the retreat, and just camping a few miles out of town for the retreat. We can always go down hill if a storm is predicted. We need only drive south 50 miles to drop our elevation by 3,000ft (914m), which would result in a pleasant abiding during a winter storm.
There are additional advantages in remaining in this area, as most of the common box stores and camping equipment sources are here, as well as several grocery store options. Whereas, the other town I have been considering camping near happens to only have two grocery stores and no box stores.
Another advantage of camping near this town is there are so many food banks, and free kitchens here that anyone on a budget, who is attending this retreat, like myself, can actually acquire all of their food, and even a sleeping bag, tent, warm clothes, etc. for free, by going to the local services for the poor to get equipped. We could make it something like the daily begging rounds that Buddhist monks are known for.
So, let us know what your preferences are.