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Say I want to create a big endboss NPC but find the guidelines for NPC gear/wealth a bit puny for this particular character. How would the NPC's challenge rating change if I gave him as much wealth/gear as a PC of equivalent level? Are there rules/guidelines for that somewhere in the books?

Currently, the board looks like THIS. I'm using Opera 9.25.

Neither Tough as Nails nor Extra Second Wind allow you to use the Second Wind ability more than once per encounter. If you take both, you can use Second wind 3 times per day, but still only once in any given encounter. Your example doesn't work.

Not all PCs should be directly involved in fighting the Sith Lord. Look at Return of the Jedi. Luke does his Jedi thing with Vader and the Emperor; Han & Leia are playing guerilla down on Endor; Lando is flying the Falcon. Just having 5 PCs blasting at the Sith Lord doesn't feel Star Wars-y to...