You're probably having issues because you've sketched a bunch of different protrusions of varying profiles/thicknesses. Sheet metal operations, such as bend, jog, dimple, etc....only work on models with consistent thickness.
On top of that, you have a 45 degree bend angle (acute angle) and a 1" bend radius, which may or may not make the bend fail because it is impossible to generate such a bend given the part size (which we don't know)
Since this is obviously not a part for manufacture, you should simply draw the part the way you want it to begin with, instead of trying to use sheet metal bend commands. These you should use only if you need to produce a flat pattern DXF for manufacturing purposes. I think the bend command will trip you up more than it will help you.