Is there a specific reason it was chosen that the keyboard does not or should not follow the onscreen selection of incremental vs continuous?
Absolutely. By default the on screen buttons do not change the way any external input operates. This is intentional. I fought it tooth and nail myself for a while but have since realized it is better this way. It allows you to have multiple sources of input, each doing what they say they are going to do. For example, keyboard, pendent and on screen buttons. Each is independent from the others. Say you use Cont. Jog with the buttons and usually only do incremental with the pendant. Having them work independently when you go from screen to pendent you don't have to make sure the other is in the same mode. Also you do not have to worry with who is master and who is slave. This is one of the small things Mach4 does differently from Mach3 that adds to Mach4's incredible flexibility. With proper hardware and scripting you could customize 4 so that any jog input changes the mode for all jog inputs but I have never heard of anyone wanting to after trying it like it is.