G.I. Blues - Multiple squatters can be found in the ruined store, being supplied food by the NCR's Supply Corps. They are similar to the destitute traveler, as they have no worthwhile interactions with the Courier. They mainly serve as background characters to reinforce the setting and atmosphere of Freeside.
If the Courier decides to enter The Strip by going through Freeside, a squatter can be seen attempting to run past the robot greeter to gain entry, but he will be killed by the guards. Old Ben will warn the Courier to not attempt trespassing, as there is no way past the gate without the Securitrons turning hostile. Instead, they can talk to the greeter to inquire about accessing the Strip, which can be done by passing a credit check of 2,000 caps, hacking the robot with a Science skill check or showing a valid passport.