Apartment in Old Town, with roomate: About $500 a month.
Apartment at 1016 Chester, no roomate: About $500 a month.

Apartment in Old Town, $300 application fee, plust 1.5 month’s rent due on move-in.
Apartment at 1016 Chester, $50 application fee, no security deposit.

Apartment in Old Town, exactly where I want to live, with free washer and dryer.
Apartment at 1016 Chester, familiar place that I know is decent.

So. I need to clearly go with the 1016 Chester place, until I can afford what I want. :/ Making the smart decision sucks.