I have about 18K miles on my Model S with the first-generation sensor package. I live and drive in New England.
The lane-holding feature (autosteer) does expect you to keep slight pressure on the wheel. It has, that I can discern, four modes ...
freeway following (another vehicle in front)
freeway leading
nonfreeway following
nonfreeway leading.
Only in the first case, you have five minutes before it starts pestering you to hold the wheel. In the other cases it's one minute.
Lane holding and adaptive cruise control in freeway following mode is a WONDERFUL feature. It drastically reduces the driver's workload in heavy traffic. And, it has speed control features that contribute to the melting of compression-wave traffic jams.
Lane holding can be a little squirrely when the road surface is dirty. I think the car sometimes mistakes tire marks for lane markings. There are parts of my regular route where I just take over from lane holding.
Snow or heavy rain? the lane holding feature goes first, then the adaptive cruise control. Snow, rain, or frost on the windshield interferes with the forward looking camera. Snow or ice on the nose interferes with the radar. Ice on the bumpers interferes with the near-field sonar proximity sensors.
Autonomous driving on the Stanford campus and up Sand Hill Road is one thing. Autonomous driving in a nor'easter snowstorm on winding Atlantic Coast roads is another. We shall see.
I admire and support people who tackle hard problems fearlessly. Tesla's doing that.