Feasibility I think can be done by rules checking / constraints but cost has a lot to do with the specific supplier capabilities in several dimensions.
As a machinist , yes, let's have AI do drawings, please. Getting rid of professional drafters was a huge mistake. Modern GD&T is complicated - which brings up an inherent problem. Our system of drafting a6GD&T doesn't have an explicit mathematical model - it's just based on practice. Therefore, you need some form of systemic approximation. There's one from Arizona University that NIST seems to prefer.
The other problem with automatic drawings is design intent. Consider that you may have several ways to dimension a hole, but one of them may more clearly express design intent. Pretend we drill a hole in a cube block. For the centerline of the hole, we have two different surfaces to dimension from in each direction. Depending on how the component assembles, it can make a difference given the assumption that the machining is done correctly.
If the dimensions go left - down, when the part is in the machine, it should be setup and programmed with the references on top and left. Correctly done, the tolerancing constrains not only the size of the component but also the best practice machining strategy. Tolerancing for manufacturability isn't something I hear discussed but should be. The other question is - can that tolerance be directly measured, or will it need to be calculated on the shop floor?