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I currently live in Olive Branch. It's a nice enough area. There's no chance of walking/biking to shops, libraries, etc., but not because of crime- because the city wasn't set up to accomodate non-car travel. The city was a rural community that experienced a huge boom as people moved out of Memphis.
You'll find a wide range of home quality from subdivision to subdivision, with the newer subdivisions faring the worst, since they didn't have time to really develop before the housing market collapsed.
DeSoto Co. schools are considered the "best" in Mississippi, and are viewed as more desirable than Shelby Co. (Memphis) schools.
Olive Branch vs. Southaven is hard to find a clear winner, since both are so vanilla. Best I can offer is Southaven started booming later than Olive Branch did, so you can find newer houses that way.
In the 5 years I've lived here, I have never felt unsafe, and the sorts of crime you'll mainly hear about is opportunistic, someone didn't lock their car and so their CDs got stolen, type of thing.
Olive Branch Police Department actually has a page on Facebook, and they list all the daily crime activity if you'd like to check it out.
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