Much of the flavor comes from the wrapper, so with a larger ring size, you've got a ratio of more inside leaf to less wrapper, which can mean less flavor. Connecticut shade versus a maduro (technically 'maduro' refers to a specific color, but more generically refers to darker wrappers) will be darker and sweeter. Draw is very important; it it draws too fast the cigar will burn fast and hot and will have a bitter taste along with being too hot. Too slow of a draw and you won't get much smoke and it'll go out more frequently. How it's cut is generally an issue of personal preference (cut versus punch), but if you don't cut/punch well the draw will be too little.