smbakeresq
Explorer
Also, a familiar is an ally and understands you. It certainly would be affected by Inspiring Leader if your group has it.
In my current Eberron campaign, the group's wizard, Arthur d'Cannith, salvaged parts from an iron mutt construct named BNJ-1. He kept the name, but reworked the parts into a robo-owl familiar. He typically uses him for scouting or casting spells through him. Here he is exterminating some mutant flying kruthiks with a poisonous dragon breath while Arthur uses a shield spell to avoid their claws (art by @Valmarius).
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I prefer my wizards use their powers in interesting ways and for self-promotion rather than just cheesy tactics.
Case in point, that same wizard in my campaign uses prestidigitation to make a poof of smoke whenever he arrives or leaves some where. (You usually get a quick glance of him running away from the smoke to 'complete' the illusion)
I wouldn't call that a certainty. The feat was designed to work on creatures of roughly human mass, by giving them an amount of tHP not greater than a quarter of their total (since you need to be level 4 in order to qualify for the feat). An extra 5 tHP to an owl with 1hp is a lot more than an extra 5 tHP to a humanoid with 20hp. It sounds like a prime case for DM adjudication.Also, a familiar is an ally and understands you. It certainly would be affected by Inspiring Leader if your group has it.
Likewise, the Help rules were written for use by someone at least as large as a halfling. I wouldn't allow a tiny owl to grant Advantage on the barbarian's attack roll against a dragon. The owl can't meaningfully affect the dragon in any way, and it is beneath notice.
Maybe the familiar "helps" by pointing out weak spots in the dragon's armour?
Yeah. So the familar flies within 5ft on the dreagon and marks the spot of a missing scale. Then flys away. So everyone gets advantage on every sunsequent attack...
I'd rather allow you to take disadvantage on the attack roll to try and give you an automatic critical hit.