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The HD shocks tend to fail faster with lowering springs because they're designed for stock ride-height so they're not getting their full designed travel and rebound curve. Regarding the 255s, that width on a 9.5" wheel is very far from "meaty". Truthfully they'll be a little stretched.
Regarding your speedo question, see my post in the other thread. Going slightly taller won't be a problem.
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