First of all, you are mistaken about the Cold Weather Rule. It does NOT prevent a landlord from evicting a tenant, or refusing to renew a lease that expires during this “cold weather” season (see
here and scroll down to #26).
Now, how long it takes for the Bailiff to set him out depends on the timing of the courts, when paperwork gets filed, etc...
Has he been to court yet? If so, where is the case at? Foreclosures, from beginning to end (set out), can vary from a few months to a many many months...and I've even seen them take a couple years.