Changed the oil in our main daily driver, probably was a bit earlier than strictly necessary but it was past the service mileage stipulated in the manual and it’s above freezing finally. Managed to not make a mess and didn’t run into any issues. Even torqued the drain plug to within spec. Then got it washed to get rid of the salt crust from the past few weeks and wash out any oil drips from the filter the got on top of the plastic air guard.
I considered it, but decided against it.
Fun fact: There’s no flat surface around my house for doing it. Nor is it sheltered, and it usually rains sideways where I live. So my usual place to do these things is inside a 2km long mountain tunnel 5min drive from my house. There I can change oil, brakes, seasonal tyres, with no wind or precipitation, and temperature above freezing. In the middle of the tunnel there is a large excavated space on the side of the road where the snow plow turns around, so it’s not like I’m blocking traffic either.
Luckily we have a garage that’s perfectly sized to get the car on ramps and close the door. I still lay on cardboard since the concrete is cold (and to catch the errant drip). When we lived in an apartment in the city I’d usually bite the bullet and take it somewhere since we couldn’t do any car work in the parking lot. In the past I’d take it to a buddies house but then moved a few hours away so that wasn’t a choice until e bought a house a few years ago.
You don’t need a flat surface. I do mine in my sloped driveway. Just be careful with the jack (or use ramps) and be sure you’re filling with the proper amount. Can’t help much with the weather though other than suggesting you get really fast at it (I can do it in about 10 minutes easily) and use some scrap cardboard boxes to lay on.