Hi-I have never heard the outlaw either but have some limited experience with sherwood.I think the outlaw would be better-but how much?outlaw has more channels,if that matters.better bass management in the outlaws-good if you have different size speakers front and back,or if your having trouble with your bass.However,I think the sherwood amp uses push-pull circuitry which brings out the detail in the sound-so the outlaw amp might be a letdown in that regard.Basically,if your generally happy with your sound and don't want more channels,you might be better off sticking with the sherwood.If you want possibly more power,or updated features you might want to upgrade to outlaw-but I wouldn't necessarily expect earth shattering changes.