Manhattan is not a very family-friendly city for anyone but the wealthy. I can’t remember a time when I didn’t know that everything in Manhattan is over-priced. Stores sell groceries in small packages because both they and their customers have limited shelf space.  The small sizes used to run the same as the larger family-sized packages elsewhere.  In order to make life in New York more affordable, we, and many people we knew, went to New Jersey for clothes (no sales tax on clothing there) and the suburbs for groceries.
When I first moved to Portland, I was shocked at how affordable everything was.  I even contemplated buying my first house at age 18 because housing was just so affordable it was hard to resist.  Given how much housing prices have appreciated, one of my few regrets is not having acted on that instinct.
I spent my senior year of high school working for a theatrical agent.  [Point of pride: she is Tony Kushner‘s agent and picked him up before Angels in America.] One of the things I did for the agent was go see some off, off, off Broadway productions as a initial filter.  It was a fun way to see some great theater that I would have otherwise missed.
In the days before Measure 5, Portland was filled with small theater companies.  Tickets were so affordable that even a college student could afford to go out several times a week (assuming the student had the time, which sadly, I did not).  Despite my time limitations, I was fortunate enough to see some great productions before budget cuts decimated Portland’s theater scene.
During my time in Philadelphia, my best friend and I used to go to New York a few times a year on what she called “Theater Weekend Extravaganzas.” We would rent a cheap hotel room on Hotwire and go see as many shows as we could fit in to our weekend.  Most of the shows were off or off, off Broadway, but we usually managed to squeeze in at least one Broadway show.  Those weekends were expensive, but not jaw droppingly so.
David and I are planning on heading into Manhattan tomorrow and were trying to decide what to do.  Since it is a Wednesday, we were thinking of maybe catching a matinee of Kinky Boots.  When I priced the tickets, however, I discovered that it would cost the same for the two of us as an entire weekend of theater used to cost me and my best friend.  In theory, we could have gone into the city today, waited on line and possibly gotten half-price tickets to tomorrow’s matinee.  But that would have taken more time, money and energy than we wanted to expend on this particular show.
Instead, we will go to a museum (we are still debating between the Museum of Natural History and the Met) and entertain ourselves that way.  Then, when we get home, we will satisfy our theater cravings by going to see some shows at the Broadway Rose and Lakewood Theater Company that are both good and affordable.