From SI-1505:
"The use of pre-heat will facilitate starting during cold weather, and is required when the engine has been allowed to drop to temperatures below +10°F/-12°C (+20°F/-6°C for –76 series engine models)."
If you run Multi-Vis oil, you are better off w/r/t cold weather starting.
Lycoming SI-1014, Rev M, gives recommended oils.
With my O-200 VariEze, I run straight weight oil, and I preheat as the engine temperature (when cold) gets below around 40 Deg. F. I use the carb temperature gauge to make the engine temperature determination.
I'd talk to Ken Miller for excellent information on engine operations - Ken is an engine Guru, and deals with cold weather ops (he's based on the East end of Long Island, NY).