As my flatmate plays Kirai and I field the Vickies this is the one matchup I feel to be kind of experienced with.
First of all - I'm rather surprised with your list. I usually go for the magic weapons and a librarian. Still, we mostly play 35ss
As it's been pointed out quite a few times Kirai will need some muscle. That being said (always depending on the stragies and schemes of course) I wouldn't recommend going for the Vickies. Personally I struggle the most when Shikome and/or Ikiryo manage to kill off something early in the game. In my case it's usually the librarian or the student since you can hardly keep them totally safe from a well placed Shikome.
Other than that it's Johan or Taelor. They aren't easily defeated but especially Johan tends to get worn down by a number of Gakis.
The two faults the Kirai crew can't afford is 1. leaving her too far behind to regain Seishin and 2. spreading too far and thus allowing the Viks to do slingshot kills.
The Vickies, however, tend to survive really long which commonly nets me bodyguard. My friend has more or less decided to leave them alone and leaves me sitting on some soulstones. Still I can hardly play them more offensively since that would mean to slingshot right into the heart of his crew, whirlwind down as much as I can and hoping to somehow survive his backlash - which is highly unlikely. It's quite a stalemate: He goes for bodyguard as well, knowing that nothing except for the Viks has a mere chance of taking down Kirai.
So usually the game is decided by the first big losses and how this affects strategies. Most times it ends with Kirai and her Seishin-Shield (or whatever she has summoned turn 5 or 6) on his side and the Viks plus something that's managed to survive (often it's Taelor) on mine.
I recently got Misaki to try a totally offensive approach (like Viks, Johan, Taelor, Misaki and something to fill the rest). We'll see how that goes...
-DoT