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Alright, I'm kind of sad that Kotomine doesn't get a lot of spot light. I mean, he manages to pull of all he does and doesn't get his recognition? Rin is getting way too much attention compared to him. Just because she is such a supposedly cool master, nothing against her popularity, really.

Kotomine is the Judge of War, that is a really wicked position to be in. Not only was he in the last war, he managed to keep his servant. A pretty powerful archer servant to be exact.

He manages to do a few very tactical moves:

Tricks Rin with his deceptive nature. Doesn't even suspect him until he stabs her.

Even harms Shirou while not displaying his grudge. He even kills Shirou's adopted father for crying out loud! Kiritsugu suffered because of that nice black goop that was the corruption of the Holy Grail (Angra Maiyu).

He even gets Lancer and sends him around. He said he was a previous master, but never said anything about a certain King of Heroes still existing.

He also takes Illya and tries to make her the Holy Grail.

If that doesn't make him the better master, then I think we have a few problems.

Kotime Kirei...The man certainly is the most acomplished of the magus in the 5th war. However, (and here's where the spoilers come in.) he was involved in the forth war but was only a putppet for Tokiomi Tohsaka. He was to oversee Tohsaka's victory with his servent or rather servents. He broke the rules in the fourth war and summoned Hassan I Sabbah. His servent was Assassin. Tokiomi's was Gilgamesh. Also, Rin has always distrusted and never truely forgiven Kirei for her father's death in the fourth war. Not to mention that Kirei basically taunts her even when she was a child. The man has a long list of acomplishments and his use of somewhat dishonarable means can be taken into a Machiavelian view and dismissed as necessary.