a Holiday Inn road book/to pick up $150/all across.

[Vladv1]

Ian Jeffery: ‘We’d be trying to pick up $150; driving along with a Holiday Inn road book in the front of the car for directions. No travel agent. And Doug would tell us to go back to where we’d just come from cos they wanted another night from us.’ They would pool their ‘shitters’ – small bills and loose change – ‘to see if we had enough cash to scrape together a Dairy Queen’: a meal at the cheap-and-cheerful fast-food chain then dotted all across America’s freeways.
Mick Wall, "Hell Ain't A Bad Place To Be".

What does "to pick up $150" mean in other words? Does a "Holiday Inn road book" mean that the hotel produced its own maps? What does "all across" mean in other words?

 

[emsr2d2]

"Pick up" means "earn" or "obtain".
Yes, it appears that the Holiday Inn company produced some kind of book in which it listed every Holiday Inn in the country, along with directions to each one.
It's easier to read it as "all across America ..." so it refers to the Dairy Queen fast-food chain branches that are dotted all over America, and they were specifically hoping to eat at the ones close to the freeways.

 

[Vladv1]

"Pick up" means "earn" or "obtain".
Yes, it appears that the Holiday Inn company produced some kind of book in which it listed every Holiday Inn in the country, along with directions to each one.
It's easier to read it as "all across America ..." so it refers to the Dairy Queen fast-food chain branches that are dotted all over America, and they were specifically hoping to eat at the ones close to the freeways.

What does "cheap-and-cheerful" mean?

 

[Tarheel]

What does "cheap-and-cheerful" mean?

Why don't you take a shot at it first?

 

[Vladv1]

Why don't you take a shot at it first?

Cheap but tasty?

 

[Tarheel]

Cheap - relatively inexpensive
Cheerful - welcoming; not grouchy