We run seven flight training aircraft, all Lyc-powered. Four are O-320s, one is an O-540, one an IO-360, and one an O-235. We store them in a hangar heated to +5°C (41°F), and that's where they'll be started, max, on a winter morning. After that they sit outside and are blanketed until the next flight, unless it's pretty cold (-15°C/-5°F) and they sit too long. We don't fly them at all below -25°C/-13°F; the CHTs and oil temps just won't come up enough for safe operation below that, and they'll tend to quit in the overshoot after an extended glide.
Only one of these engines minds this treatment. The O-235 has low CHT and oil temps anyway, even in the summer, and condensation in the case and on the cylinders causes corrosion that results in excessive cylinder wear, requiring a top at about half TBO. All of the others make it to TBO with the compressions in the high 70s and no metal in the filters. These are training aircraft, remember: frequently flown but often abused, and make TBO even without preheating below 40°F as so many pilots think is necessary.
We use Aeroshell 15W50 exclusively year-round. The multigrade allows oil to flw at lower temps; too many cold engine wear problems are because guys are using 80, which stiffens up and the pump can't suck it up from the case very fast. Put a jug of it in the freezer sometime and see how it pours. Big mistake: running the RPM well over 1000 right after startup when cold. No lubrication once the pumps starts cavitating.
The Aeroshell also has the Lycoming LW16702 additive in it to stop cam and lifter wear and we have absolutely no trouble with valve train problems. We used to have such wear when using other oils without the additive.
Our biggest hassle with cold starts involves too much prime, which just floods things and wets the plugs, or priming too early, with the prime condensing on the intake walls and running down into the carb. Prime should happen immediately before cranking. And if, with a really cold engine, the engine starts and then quits and won't catch again, the plugs have frosted over with the moisture from combustion and they'll not fire any more at all. You'll just kill the battery, and a dead battery's freeze point comes way up. It'll freeze and split.
Dan