My biggest challenge in zone three is probably pretty obvious. It's trying to get everything done in such a short time frame between frosts/cold weather. I clean up as much as I get time for in the fall, before the ground freezes but I also have to mulch everything, so I usually have to do most of the cleanup in the spring. I try to move things around, plant any new perennials, and dig some things and pot them up for a spring plant sale that I have whenever time allows.
Right away in spring the vegetable gardens have to be made ready and cooler weather things planted but it's always pretty iffy to plant the warm weather plants before June first. Then the planting of flowers and summer bulbs and re-mulching where you planted them. Then the planting of whatever containers you're doing. Meantime you have to be keeping all this watered, if it doesn't rain, while your doing your other plantings. Of course there is always weeding and deadheading and taking care of the vegetables as they ripen.
Then there is the taking of cuttings for things in the fall and digging and storing the summer bulbs. All of this has to be done in about four months take a week or so. I have a lot of gardens so it does keep me on my toes trying to get everything done!