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With that said though, I'm not overly impressed by any of the companions quality.
Also him misleading you isn't similar to being demonic. Demons are self serving whereas Regill is not for example. This is more of an issue with how reductive the alignment system is than with Regill as a character.
And yes, he is also pretty hypocritical. I don't know if his crass comment on Irabeth's breakdown is necessarily hypocritical - he may have been killed by the Gargoyles, but they didn't break his spirit. Nevertheless, he is always going on and on about obedience to your superiors, accepting authority and keeping strict discipline. He's always quick to suggest harsh punishment for any sort of disobedience, but that apparently excludes himself as he undermines and manipulates you on every turn on his personal quests. You can say he just does not accept your authority and does not consider you as his superior, but you are.
Spoiler for the end of his personal quest -
On my Azata playthrough I've banished him right before going to Threshold and the secret ending. The game does give you the satisfaction of using him and then dumping him. It's even better than killing him. Just reading the secret ending epilogue slides and imaging his reaction for narrowly missing that due to his inability to be loyal to you. Get lost Regill, get lost.
as for him getting feeling sick from the chapel thing.... he makes it clear in a earlier conversation that he is constantly striving to make himself more like a construct... pretty much its an ongoing goal kinda thing... he doesnt come outright and say he is "without emotion" but strives to keep it in check constantly.... we dont see in game but for all we know he could have went off somewhere and gave himself lashes or something after lost chapel...
also the whole 5th crusade thing and mocking it... doesnt seem hypocritical... I mean the hellknights are the hellknights... they are constantly fighting the war... whereas the queen has had 5 crusades where she would unite armies together... waaay more resources than the hellknights could muster im pretty sure... and so after 4 crusades that gave big promises to only do very little or fail horribly.... the queen even admits how hard it is to keep the spirits up after all the failures and when your character comes along and performs a miracle her hands were pretty much tied into appointing you knight commander in order to unite people again... in the hellknights eyes the crusades have been nothing but an undisciplined chaotic mess...
Edit: moreover, what Regill actually does is not "assisting as long as his goal align". If the Crusade no longer serves the Hellknights goals, there's a lawful, straightforward procedure of terminating the partnership. He does not bother with any of that. He does not even give you a warning you're straying (at least in the mythical routes I've done - all the good ones + trickster). Instead, he's pretending to be loyal and deceiving you to get his way and put you in the Hellknights mercy. He'd immediately execute any of his Hellknights for this kind of disloyalty, and he probably tells you that himself if you're going for killing him at the end of his last personal quest (I never did). He just believes that his superior intellect and judgement allow him privileges he does not give to anyone else. Hence, hypocritical.
There's no hypocrisy here. Additionally it might depend on how you play the quest through but when I did it the rest of the Hellknights were in on Regill's "competence test" and assisted him in it so obviously they were consulted.
What are you talking about? As in what actions does Regill take that caused you to type this section. I have only played through it the once.
Also your mention of following a "lawful procedure" implies you have the wrong idea about what being lawful in D&D means. Lawful in D&D and so pathfinder means sticking stringently to whatever principles you follow, not to any legal procedures in an area you are in (though if they do not contradict lawful characters will normally also do the latter).
For example if you are a member of an organisation dedicated to destroying the worldwound allying with another group while they are working towards goals that also serve your own and then immediately and efficiently abandoning them if they stop or destroying them if they start to work against you would be lawful because all of your actions are working towards the goal of your organisation which is destroying the worldwound.
That's not actually true. There is no action that a lawful person is not supposed to do. Lawful or not lawful comes down entirely to following the tenets of the belief structure and/or organisation you are part of in D&D/PF.
According to this flawed logic demons can be lawful too, when they follow the tenets structure and/or organisation of Deskari/Baphomet/Lamashtu/Nocticula's cults. Any loyal Baphomet follower - say Hosilla - is lawful according to this absurd definition.
Edit: plus, Regill isn't following any "tenets of belief" when he's lying to you other than his personal (mistaken) belief that he knows best about everything so he has the right to judge you and get rid of you if you're found lacking.
Especially his comment towards Nurah when she goes on a rant how bad she had it and justifies joining the demons was particularly satisfying to read.
No since Arcanum I've always hated Gnomes and went out of my way to not interact or brutally kill them, but Regill won me over.
actually when I met him it seems pretty clear in the beginning what his goals are... he openly mocks the idea of a "5th crusade"... and how he heard about the main character who was able to turn the tide with the wardstone issue and was interested in the rise of a new um... forget what he called it... but like a new piece on the chess board kinda thing.... and he also boldly claims how his order doesnt answer to even the queen herself....
putting all that together it looks like to me he is only interested in you and what your capable of... if he really was gonna follow the command structure then the chain of command would be the knight commander... which answers to... the queen.... she is the only one who has the authority to discharge our MC afterall.. she appointed them to that position... and before Drezen he doesnt make a decision to stay for the whole crusade only help assist with retaking it for a tactical advantage for the hellknights to regain some outposts deeper in the worldwound...
and in the beginning when you rescue them from the gargoyles if you pass the perception checks when he's giving orders he's watching your reactions... measuring you... a person that is able to perform miracles and a strong power to push back demons... while the crusaders and all might think its a blessing from the gods... he is more reserved in judgement... no one knows how or why you have this power and im sure he would wanna make sure that you are a asset and not a trojan horse i'd imagine...
It's not flawed logic. It is flat out how the rules work. As for oddities like this the demon itself can be chaotic (somehow) but if you worship a demon if you perfectly mimic its actions/beleifs you would actually be lawful as you're sticking to your beleifs, even though the demon itself is chaotic and most people would call the follower chaotic as that is intuitive.
It's a basic problem with D&D's alignment system. It doesn't really work. In practical terms you're just supposed to go with whatever your DM says to get around oddities like this.
Also Regill is following the order of the godclaw because he is a hellknight. Godclaw is all about eliminating chaos.
It's better to think of the axis as being chaotic/evil is self serving and lawful/good is selflessness. It's not the way the rules are written to work and it too doesn't reliably work but it is more fitting than any other way of trying to interpret it.