$450 - HUGE room in a groovy multi-generational house - CLOSE IN!! (SE Portland)
The appeal: The promise of a funky craftsman with a "quick walk" to bars, shops, a New Seasons, and the Willamette River is pretty enticing for only $450 per month with no lease or deposit. You're not entirely sure what "groovy multi-generational house" means, but it can't possibly be worse than living with a bunch of 22-year-olds who still think it's funny to blast one another with the fire extinguisher at 3am every Friday night, which is what you're putting up with now.
The reality: The house is indeed picturesque, and only four blocks from the Willamette... but it's all the way in Sellwood. You soon find out that "groovy" and "multi-generational" is a reference to the negligent ex-hippy divorcee proprietor of the place, who allows your other roommate -- her teenage son -- to act like a maniac at all times.
The final straw: After politely asking the kid to stop stealing your smokes and drinking all your coconut water, you tell his mom about his bad habits in hopes of recourse. Something. Anything. She disciplines him by revoking access to the brand new Toyota Tacoma his absentee father got him for his 16th birthday, to which he retaliates by stealing your wallet, hacking your car2go account, and crashing a smart car into the front window of an Arby's in Milwaukie. You quietly disappear in the middle of the night, more bummed about Arby's being closed than any other outcome of the scenario.