Have 2 blend files. what direction should i go?

hi all im trying to model something and i feel like something is wrong. i have 2 examples of directions i can go and the second picture is the one that seems right but looks worse. or if you guys have a different way i can do this. any advice on the best possible way to make this? ive spent quite a lot of time trying different ways on this shape and it can get real ugly. these are the least ugly ways ive got. thanks if you can help me

https://www.dropbox.com/s/a73n6oh0ydte4xf/exampleblend222.blend?dl=0
https://www.dropbox.com/s/57jddq3siffzvxb/exampleblend111.blend?dl=0