I agree, lifting up to the top of the hood is not fun. I did that for years.
It depends on how much you use per year.
I went to a 55 gallon drum for a while, but that was a hassle getting it out of the pickup truck and didn't last long for me (I have a one tractor and a skid steer with 28 gallon tanks).
I went to one of the 250 gallon cubes and have been very happy. I would suggest putting a filter on the pump.
Around here, there is a 150 gallon minimum for delivery, so the 55 gallon drum wasn't enough.
Winter storage isn't a problem although you probably want a winter blend rather than a summer blend diesel fuel. If diesel sets too long in warm weather, especially if there is moisture in it, algae may grow. Hence the suggestion of an inline filter.
If you don't use all that much, perhaps a 55 gallon drum only half filled would be an easy approach. Although diesel should be good for a couple of years, I would prefer not to have it sit for more than 6-8 months.
Ken