Sharpness is a complicated subject, but DOF less so. It really is just a calculable value--with certain subjective assumptions to be sure, regarding "normal" print sizes and "normal" human vision, incorporated into the value used for acceptable CoC--but there really isn't any need to get worked up over this topic.
DOF is always calculated relative to focal length, aperture, subject distance, and format, based on print sharpness, so enlargement factor is included in the calculation. Format is expressed in the calculation by the value chosen for the acceptable circle of confusion.
Experience and taste come in when you consider whether or not to accept the standard DOF value when you decide what aperture to shoot at. Say you plan to make a very big enlargement--if you're the sort of person who calculates these things, you might use a smaller value for acceptable CoC than what is normal for the format. If you just use the DOF scale engraved on the lens, you might decide to stop down one or two more stops than the scale recommends, and you would be doing the same thing.
For those who want to try running some numbers and reading about the formulas used to calculate those numbers, I recommend a shareware program called "f/calc." The formulas used by the software are in the help screens, and they are explained more clearly there than I could do here.