Finally, found the magic option that wasn’t getting enabled in the kernel config. It’s been hit or miss whenever I tried to configure a new kernel whether the wireless would come up the first time.

Module Size Used by
michael_mic 2176 2
ieee80211_crypt_tkip 9536 1
ieee80211_crypt_ccmp 5888 1
i915 18880 2
drm 64084 3 i915
ipw2200 126260 0
snd_intel8x0m 12748 0
snd_intel8x0 26268 2
snd_ac97_codec 88292 2 snd_intel8x0m,snd_intel8x0
ac97_bus 1856 1 snd_ac97_codec

michael_mic (from the crypto section in menuconfig) is required for tkip support to work.