The first encounter is the start of the game and is very easy, ie: its the tutorial
Finish the prologue is short and it ends with you getting a drone

Getting 2k is not hard you will probably get it by the end of the story. if not rob the richer houses like 109 or buy all the tips for loot in the neighborhood.
Getting 5k is most difficult, but if have the atm hacking device its easier. all you need to do is rob the atm which will get you around 2.5-3k and then rob it again after its filled up.