[TakeiT]

You need to use the function random. Go to the places that you want the checkpoint to possibly be and type /save to get the data then put it into an array. From there, you can use a random to get one id in the array and set the checkpoint to that. You can also use random to get the amount of cash.

https://sampwiki.blast.hk/wiki/Random

They use random spawns as an example here, but it's pretty much the same thing