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After 10 years of playing, I finally decided to learn about NPC skill trainer limits. You can train 5 total skill points per level. Power train early by talking to a trainer
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Skyrim:Lockpicking - The Unofficial Elder Scrolls Pages (UESP)
the elder scrolls v skyrim - How often can I pay to train skills? - Arqade
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Skyrim Thief Skills - how to max Sneak, Speech, Pickpocket and Lockpicking | Eurogamer.net
Every Trainer In Skyrim (And Where To Find Them)
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