C18 -> C8 -> C4 -> C1 -> Phenyl
Strong retardation -> low retardation, so for compounds with very high RT on C18 it can make sence to try a Phenyl column. Most problems come from a long equilibration time, very sensitive to buffer changes.
I would not approve the classification of phenyl columns in this sequence generally. You might be right when considering only hydrophobic interactions, but when pi-pi interactions come into play (and that's what phenyl is good for) phenyl vs. alkyl might look completely different. Then you migtht actually get more retention from phenyl than from C18.
Also, when long retention times are a problem, I'd rather stay with alkyl and go down to C8, probably C4, and not necessarily to phenyl. I usually try phenyl only when I just cannot get enough selectivity from C18.
Concerning longevity and reproducibility of phenyl, I'd say if you don't abuse your columns there's not that much difference anymore between good modern phenyl and C18 columns.