Getting this achievement is really easy: you need to sleep in the dumpster behind Whirling-In-Rags.
Take note that this will end your current run, so make a save before that. You do not need to have Hobocop opt-ed in or internalized.
Three conditions need to be met for the related dialogue to appear:
1. Day 2
2. Argue with Garte about wanting a free place to sleep after 10pm [C1275D1307]
3. Do not change your mind about sleeping in the trash container
After that, the option to sleep in the dumpster should become available to you. Doing so will trigger the achievement and end your current run.
Credit to
xyrilyn for their
guide.