On my E350 I must be careful about the rubber seal on the old filter. It tends to stick to the engine rather than the filter; then when I screw on the new filter there are two rubber rings and leaking. One time I got the old filter stuck on. Maybe I forgot to grease it or tightened it too much with the filter wrench. That was messy - removing with the filter wrench broke the filter so the wrench was unable to get a grip. I drove a big screwdriver through it to turn it off.
A large funnel with outlet nearly as large as the oil filler cap makes pouring oil in much easier.
I agree, a good time to also have a good look at rubber radiator hoses, snow deflectors, give the front end a bit of grease, check brake and steering fluid levels and clean or replace the air filter.