lparkslp I am also in Zone 5. I will winter sow for my perennials in jugs in a couple of weeks from now. And then my vegetables and half hardy annuals in mid to late March thru late April.
Type of vegetables I do by winter sowing is Squash, Cucumbers, Tomatoes, Celery to name a few.
Annual flowers that do well for me are Zinnias, Marigolds, Calendula, Celosia and many more.
I find the biggest killer on winter sowing is the plants die from lack of water. Need to watered regularly. Putting your jugs on top of dirt helps as wells putting in tub etc with dirt on bottom that hold moisture longer. I will also cover my jugs in plastic at night for more warmth later in the growth to keep them growing good during our late in season cold spells.
I cut my milk jugs about at about the 2/3 to 3/4 mark and fill with dirt to about 1/2 way mark. Want to get some good root growth.
Been doing this for over 5 years and love it. It frees up the racks inside so I can try temperamental seedlings and special tropical seedlings. And with this year swap have lots that need to be grown inside as well wintersown. Going to make for great adventure this spring.