Britney's songs now aren't even that high. The highest she goes most of the time is a D5/E5 and she has shown herself capable of singing those notes live. Britney's problem has never been range but her poor breath support. She doesn't sing from her diaphragm, she sings from her throat/head and doesn't take enough breath so she always ends up sounding winded. It's not the songs themselves that are the problem it's her technique. She has certainly sang higher then a lot of the material she has been given the last eight or so years for her albums. Britney herself has even stated that her songs aren't that difficult to sing and that she has never been challenged vocally by any of her songs, and that was back in 99/00 when she had more demanding songs like Stronger, Overprotected, Lucky and Oops! to work with. Britney's material post Zone is a cake walk because it features virtually no belting. The only thing asked of her is a few low notes, an occasional high note in head voice and her general talk-singing range.
It's not that the songs are hard to sing for her. It's what you mentioned about her poor singing style she adapted to from her record company. It's pretty much impossible to sing through your throat and give the singing style her company wanted from her while dancing. So that's why she doesn't sing live much. All these years from that nasally singing style left her voice sounding really high pitched and babyish.
I find that Ke$ha has trouble performing 'TiK ToK' but I find her performances of the other songs rather solid!
I feel like she can cover this well nowadays... From all her performances, she has most trouble with your love is my drug... Also I hate the vocoder performances of we r who we r and take it off... her own voice on these>>>>>
Alicia Keys can't sing Try Sleeping With A Broken Heart and sometimes sounds a hot mess singing No One. She never hits the high note in the chorus of Teenage Love Affair either.
Beyonce can't sing Resentment, Listen, Get Me Bodied, Freekum Dress, Green Light, Love On Top, 1+1 or I Care live from what I've gathered.
Christina can't sing Fighter, I Turn To You, The Voice Within (full song) & Not Myself Tonight. She struggles sometimes on hitting the long high belts on ANOM & Candyman.
P!nk struggled singing Nobody Knows.
Brandy can't sing any of her hits it seems like outside of Almost Doesn't Count and Right Here (Departed). She can sometimes give a good vocal on What About Us if she slows it down enough.
Mariah can't sing Forever, Butterfly, Can't Take That Away, We Belong Together, Don't Forget About Us, I Want To Know What Love Is or any of her ballads that require belting and an impressive vocal.