I ride by Jester all the time, it's a serious hill. Notice I say I ride 'by' Jester, not 'up' Jester. I don't think I would get up it on my road bike, but maybe on my mtn bike. It's on my to-to for this year to try it on my road bike.
2222 isn't too bad to ride on the little stretch from 360 up to jester (nice wide shoulders).
I ride mostly out west/north parts of town (620, bee caves, jollyville, parmer, etc.). Most of the hills are gental rolling. There are a few side streets we hit sometimes that go over 10%, but most are pretty short.