when is it time to go oversized on valve guides?

not sure i have the best understanding, when is it time to go oversized on valve guides? i have one guide bore that is broke out on port side, there's a ridge within but the taper portion went away. but guide seems to be seated good and tight in bore. used loctite to assist. I know the circlip, to an extent, prevents the guide from being pulled through. 

also, are apes better that kibblewhite guides? much thanks ia