There are two playground-equipped parks roughly the same distance from me – say, half a mile-ish.  Both involve crossing busy streets and going past homeless guys with signs and/or college students with petitions. (There are closer non-playground equipped parks.)

Park 1 is close to a famous bookstore and a great cupcake shop. It’s also got old, crappy equipment and a large population of homeless of the drunk, probable ex-con and ex-mental institution variety. Police patrol on horseback. It is also across the street from a charter school, which uses it frequently as a playground.  It has swings.  Parent friendliness rating: 8.

Park 2 has nice, new equipment.  It is close to great shopping, but I would have to walk five extra blocks to get to it.  Uphill.  It has yuppie moms and dads.  It has bathrooms (which I wouldn’t use).  It has a large population of homeless, probable IV drug using variety. Police patrol in cars (directly through the park).  It also has art students, and a dog off-leash area.  It does not have swings, but has great climbing equipment.  Parent friendliness rating: 4.

Some days, it really is a toss up.