It was apparent at the time that Steve Jobs was not a good executive nor understood the computer market at the time. Jobs’s vision ended up aligning better with the market when he went back, but it didn’t fit during the 80’s.
It depends on what the checkpoints are and if they are a drag on interstate commerce. For a while, California had staffed border checkpoints to look for produce that could bring pathogens to the state.
I always took it as Benny being a dream, someone informed by Sisko, the Prophets, and the Pah-Wraiths.
I think it is important that the Prophets picked someone who was very aware of humanity’s issues with discrimination and could rely on knowing the lessons learned from humanity to help Bajor transition.