I'm running Windows 7 on two 256GB SSD's configured with RAID 0 and they're smoking fast! Haven't really been using this set-up long enough to see any speed degradation. Don't even know if the drives themselves support TRIM.
Allie's also been running two 256GB SSD's configured with RAID 0 but on OSX on her Macbook Pro and it's also fast as hell. She's had her system about 18 months and hasn't seen and speed degradation issues.
I'm wondering if the loss in speed over time that is supposed to be a problem with SSD's is a "theoretical" slowdown that may be noted using benchmarking software but not something you would actually ever notice?
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