I have been both victim and perpetrator of bad routing, which is probably why I have a fight with my GPS every time it tells me to pass my destination, then backtrack - I know it's because there are one way streets, but I have a deep seeded aversion to seeing my destination in the rearview. I'd prefer to turn up earlier and suffer through stop signs or traffic lights, I don't want to go out of my way. Doubtless, the GPS route is probably faster, I didn't say it was logical, it's just the result of having endured some really bad routing back in the day.
When you're planning your tour you'd do well to keep that in mind. If you're booking dates in New York, Boston, Washington DC and Philadelphia before heading out to Detroit then Chicago, make sure you make as straight a line as possible. For example: Washington DC, Philadelphia, New York, Boston, Detroit, Chicago makes the most sense, depending on where you're starting. Also make sure to check the distance between cities, you don't want to go from Boston to Detroit without a day off in between. Here's a handy interactive routing map https://www.routexl.com/
I've been on tours that had us going from New York to Chicago then Boston, then Detroit - it was a nightmare! Not only are you getting frustrated with cabin fever, you're spending extra money on gas, tolls and vehicle wear and tear. And the coffin/sleep quarters on a tour bus are bad enough, but if you're travelling in a car or van? Yikes!
The larger the tour the less available the venue, so bad routing is sometimes hard to avoid. You should always book well in advance and always remember that every day off costs you in rentals, salaries, per diems and lodging. However, unforeseen circumstances do come into play; a vehicle breakdown, bad weather, food poisoning. (*Tip* Denny's is pretty reliable and most likely not out of the way.)
When you're travelling between cities you're going to be up close and personal with your bandmates and crew. Personal hygiene will play a paramount role, as will all peccadillos. You might not want to listen to the same music, or listen to music at all, that's why God made ear buds - of course that puts a bunch of people in tight quarters completely ignoring each other - but sometimes that's a good thing.