Thank you for writing and for the photo.
Could you confirm the direction of the facing of your house with the compass on your cell phone please.  It looks like your house may face WNW rather than W.  This makes a difference in MN.
First, your front yard is great.
Second, your terraces make for some very interesting design options even as they restrict what you can do without extensive landscaping to redig the terraces.
The big issue with your proposal is that it may violate the right place right place  rule. 
For example, hostas scorch.
Row 1 (Closest to sidewalk): Hostas   is in full sun (not its favorite)
Row 2: Clumping Sedum (~1ft in height)  can handle a fair amount of sun as long as it gets water for its succulent needs.
Row 3: Nepeta (~1-2ft in height)
Row 4: Russian Sage (2-3ft in height)  full sun and dry
Row 5: Gap across the lawn for mail delivery   A postman's path is brilliant and much appreciated. It should match a similar path with each neighbor (I use medium pine bark to denote the trail. As it degrades it adds organic matter to the soil.  Under no circumstances use rubber mulch.  Gravel is permanent except in your case where it would tend to flow down hill. 
Row 6: Tall native grass (3-5ft)  These would shadow the hydrangeas which would affect the curb look.  I would suggest putting them as a scrim against the house, a backdrop for the hydrangeas.  This would also produce a better effect in the winter. 
Row 7 (Next to house): Hydrangeas.

Now lets consider pollinators.  Make a graph of the bloom tmes.  Hydranges are spring with a fall bloom. But the varieties of hydrangea vary. Sedum blooms late, Sage is mid summer,  Nepeta is late summer.  As you can see, you are missing spring and early summer when pollinators are starving.  Perhaps there is more to your plan.

Finally, design.  I suggest that you do this first.  Put a table, umbrella and lawn chairs to the left side for the front door looing from the street.  I cant tell what that plant is in front of the windows of that side and whether you want it (if not take it out) or if you do whether it can be salvaged by rejuvenation pruning so that it did not block your windows.  I would need a close up of it and your intention first. 
The main reason I am sending you out for happy hour in your front yard is for you to get a feel for how the space can flow, instead of regimented lines. Take some garden hose, lay out some curves that drip and drape across the terraces.  Kick them around for week until something clicks.  I am here. Write back

Hi Caleb, 
Work out your plan for a bit.  Consider going tall to short on the left narrow side of the lawn and short to taller on the back.  Remove the bushes against the house. 
Consider columnar junipers (not spruce) that grow to 10-12 feet high on either corner of the house (if you decide this write to me with a species, so I can give you the prober placement.
Again using hoses lay out a sitting area in the front yard near the house and consider mild landscaping to make it level. It looks like you are on a quiet street, you might as well enjoy your new yard.
Google rabbit resistant perennials mn
visit the arb and gertens

The plants are perfect. The design needs work. 
See my suggestion.
You need to not have such linear rank order.  At the right coming out of your house is a round area for you to sit and have dinner, tea, and watch the sun go down, talk to your neighbors.

Thank you for writing back. 
Change the plan for eradicating the lawn. 

• Summer 2024
  • Mow the lawn as short as possible.
  • Solarize the lawn and remove bushes (June / August)
  • Till the lawn and dead grass under
  • Level the lawn as best we can?
  • Cover the lawn with weed barrier
  • Cover the weed barrier with 4 inches of mulch/wood chips

Solarization is clear plastic, not black. Painters tarp, weighted down is ideal. https://extension.umn.edu/planting-and-growing-guides/solarization-occultation

Thanks for writing back.  Given your extended time line, you might consider consulting Metroblooms.org for guidance on this project in the off season (sept).