Justice,
To start, I would limit the number of plantings that you attempt this spring. New plantings of just about everything will require some kind of watering more than likely to make them worth your while. I also am in zone 5b, and last spring was a great example of the importance of watering new plantings. We put in about 300 raspberry canes but had limited access to water and a number of other things further up our list to water. When the 90 degree weather and lack of rain that characterized last May came around, the canes were done for, even with the few waterings we were able to get in. Luckily we sourced the canes on site from an existing planting, but our labor was lost. With the way the climate is going, I would recommend against planting anything until you can be on the site to add supplemental water for the first year or two, depending on the plant.
Taking an inventory of the land would be a great place to start. If you are hoping to have an annual garden next year, start prepping that plot by sheet mulching. If you aren't ready to commit to a garden plot yet, you can still mow down and sheet mulch concentrations of perennial weeds like thistle. If you hope to have firewood for next year, that would be a good time to cut and buck a few trees in preparation.
How has the land been used since you grew up on it? This may in part determine the best course of action.
