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Does a familiar count against the number of "willing Medium or smaller creatures" that can be teleported or are they considered part of the caster's gear?
I think it depends on the spell and situation. If number of creatures are specified then the familiar is a creature and counts. If the spell doesn't specify other creatures, then the familiar can ride along as part of your carrying capacity.
^^^ sounds right
This came up in a game just the other day. Is there a rule that states your familiar can ride along on teleportation spells/effects that don't normally allow other creatures?