Originally Posted by
forumghost
I think you need to use paragraphs next time.
Also Kirei never put himself at risk against Medea, Fate he left her alone and she got Gil'd, UBW he faked his death and sent Lancer to help Rin & Shirou because she was becoming a threat to his plans, and in HF bug-boy set's her up for immediate death by Saber and makes her his Zombie puppet.
Kirei gives Zero fucks about his role as supervisor, as shown by him assassinating the Mage Association representative (Bazett) and stealing her Servant.
All that being said, you're right at least in so far as the war being kinda a shit-show what with a Servant from the last war hanging around, The Mediator being a participant, and a Servant being a Master.
Note that 2/3 of those were directly Kirei's fault, so again, not really interested in being a fair overseer.