Parking problems

My oldest son did take out the garbage last night. Regular readers may recall he did not take it out last week. I bailed him out, but vowed not to do it this week.
Although I did not have to take out the garbage, I did have to perform another chore when I arrived home from the YMCA at around 10 p.m. My wife’s van was parked in the driveway. Since she leaves first in the morning, I had to park my vehicle on the street, back her van out, get back into my vehicle and move it in. Then get out of my vehicle, walk to the street and pull the van in. It might not seem like a lot, but I do have a somewhat long driveway. On a freezing cold night every round trip (approximately 150 feet) is brutal. Widening the driveway is the ultimate solution, but I recently sided the house so that will not be possible for at least a couple of years. Parking on the street is not an option because it would block the newspaper box and I don’t think it is neighborly to park on the street overnight unless there is no room in the driveway.

In the meantime, I think my wife could save me a trip if she simply parked on the street and walked the 75 or so feet to the front door. When I arrive home I simply pull in the driveway, walk to the street and pull her car in behind me, saving a couple of round trips in the freezing cold.
As I moved cars around it occurred to me that my oldest will be driving this summer and I could be moving three cars around in subzero temperature next winter.

Should I try to establish some kind of household rule to straighten this out or just keep moving cars around most nights? Or Maybe you have another solution.