Britney will have the easiest only because she still have huge following on her social media + she can rebound back with some promos which she didn't do on her last era.
Since Mariah writes/composes her own music she'll have the least chance to make a comeback. Then Avril and Xtina, then Kelly and last but surely least J Lo and Britney. Their success depends on their next producer's/writer's vision.
I think that Mariah will have the hardest time out of them all because she has been around for the longest, her style of music isn't in at the moment but if she tries to follow the trends people probably wont buy into it. I think Avril probably won't ever have a hit song again, people seem to be over her. She was all 'anti-mainstream' and now she sings songs at 30 about getting wasted and acts all bratty. Maybe if she went back to her original style, but I don't think if she did she would have much success. If J.Lo, Xtina, and Britney all have good songs and promote them they will have a chance at a comeback. Especially Brit.
Edit: Oh, and Kelly will definitely be able to have a hit again. Heartbreak song wasn't that much of a flop IMO. I still hear it on the radio in NZ alllll the time
My humble opinion is that Kelly can make easily a comeback if she wanted to. She already did one in 2009 with All I Ever Wanted and My Life Would Suck Without You and it was great success. If she chooses good lead single, stops wearing awful grandma clothes and chooses decent make up and hairstyle, and makes good promo, she can easily come back swinging.
From the rest, I'd say that Britney can have another successful era. JLo can have a hit or two. I doubt about Mariah and Xtina (other than features). Not sure about Avril, I'd say she still has potential but it's hard to say.
My humble opinion is that Kelly can make easily a comeback if she wanted to. She already did one in 2009 with All I Ever Wanted and My Life Would Suck Without You and it was great success. If she chooses good lead single, stops wearing awful grandma clothes and chooses decent make up and hairstyle, and makes good promo, she can easily come back swinging.