re: Tell me about Biloxi and Ocean Springs...

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We are looking to spend no more than 400K and may rent initially to make sure we know the area well enough to make a good choice.

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$400k will get you a lot (no pun intended) in OS. The coolest houses are in downtown and the Lover's Lane area but also expensive. There are a few new, really nice subdivisions off Ocean Springs Road. The St. Andrews area has some nice homes further south. I'd also check out the neighborhood at the front of Cumberland Rd and Groveland Rd. Probably avoid Gulf Park. Checking a flood zone map when looking at any houses is a must in OS.

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I am fully sleeved and probably wont look like a lot of the moms

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Boy are you going to be pleasantly surprised.
There's a pretty significant liberal population in OS--especially around the downtown area.

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We would likely gamble on sports because we love it.

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You're going to be well set up right across the bridge on Casino Row in Biloxi.