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I drilled from the mark. That way I could ensure that the hole was where it was supposed to be, on the side where the position was critical. I have two 3/8" bits -- a brad point bit that came with my doweling set, and a perfectly ordinary 3/8" twist bit. Brad-point bits are far more precise than twist bits -- they're more likely to start where you want them to, and they're more likely to stay straight. My problem is that my brad-point bit wasn't long enough to go through 3-1/2" of wood. So I started each hole with the brad-point bit, then finished it off with the twist bit. I clamped a piece of ply on the back, to reduce tear-out.
A workbench needs to be heavy enough that it doesn't move under you while you're working, and stiff enough that it doesn't rack itself to pieces under the forces that will be placed upon it. It doesn't take many hours of planing a board or hammering a chisel for a worktable made of nailed 2x4s to come apart. Traditional bench designs use mortise-and-tenon joinery, which is strong and rigid, but not really suited for a novice woodworker who doesn't already have a bench.
Building a wine rack is usually a very common beginner's woodworking plan. Creating a wine rack is an easy plan that can most of the time be completed in a day or half, depending on how large and detailed you would like it to be. And the better news is that this free wine rack plan will let you build you a great looking wine rack for much less than it would cost.
I mocked up the two scenarios, and determined that with the plate inside the stretcher the vise would have a reach of 8 inches, and with it outside the stretcher it would have a reach of 9 inches. I decided that 8 inches was enough, and that the extra inch wasn't worth the extra effort. With the end vise mounted like this, the right edge of the top would have no overhang.