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I know exactly which house and apt complex you're talking about (I live three blocks away).
Cons: It's not entirely a dead-end; there's a staircase up to Alabama at the end, which allows foot traffic through there. Crossing Florida can be kinda hazardous, and you'll be pushing the stroller up a big hill if you want to go to Hillcrest (although you can walk to Trader Joe's, etc. in a reasonable amount of time). The canyon is COLD in the morning; don't know if temperature is a deal-killer for you. When we go through there on our morning walks, we always hustle upstairs to the sunshine on Alabama.
Pros: Someone at the apt complex decorates for every holiday (and takes the decorations down when the holiday is over!), which says to me that they have pride in where they live. There are families with kids on Alabama, and the kids ride their bikes around the cul-de-sac and play in their backyards that face Cypress.
If you're not committed to getting a single-family house, there are some nice apartments for rent on Indiana (two blocks closer to Hillcrest). You'll be at the top of the hill, so no pushing the stoller uphill. ;-) Good luck!
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