1. Others have had success. If you don't want to take the chance there is the Superior Shuttle/ or Harriet Quarles
2. Generally its wise to reserve a site on the north shore, it can be pretty over run. However by September, as school has started, you'll probably be ok with a walk in. A lot depends / varies of course on campground's in that area. For a few it's going to be quite a road walk at those points you mentioned.
3. If you're not concerned about any sort of completion agenda and just are wanting to do the wilderness section of a SHT thru hike count on ending at the Martin Road trailhead. From there to Jay Cooke is, aye, mostly walking through Duluth. Though Jay Cooke is quite nice.
4. You should be fine under normal circumstances, especially Split Rock.
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