On the "boredom" issue...
Disclaimer: I've never done an IB ride and I don't really plan on doing one.
The boredom topic came up a few years ago with a co-worker who was about to attempt an SS 1000. He specifically said that he planned his route on some superslab that he had not traveled often, if ever at all, so there would be new stuff to see. If he rode the same old interstate highways he felt that it would become tedious, leading to boredom, leading to lack of awareness, etc., etc. I thought it sounded like a good plan.
So my advice would be to ride somewhere you haven't been on your IB ride. My highest mileage days have come about by just leaving the house with no idea where I am going. If I ever did an IB I would have to plan some oddball route so that it would be over highways that are new to me. Or something like ride 1000 miles from home and take a few days to explore my way back.
I am a nationally published historian, but I can really do some dumbass shit every now and then.