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I want to level a DK from 55-85 and a rogue from 1-85. How risky is quest leveling in general? How many hours would you suggest running it on a server that is medium-high pop but low-medium for lower levels (~85)?
Quest leveling is by far the safest of all the options. I have HB questing on my characters long hours every day on a high pop server. Use Kick's profiles:
Make sure to follow the instructions and remember to put his quest behaviors into HB's quest behavior folder.
Questing is what all players do to level, it's grinding to level that will get you seen.