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1) I strongly recommend you don't use the Steam version of the game (which is actually the GOG version of the game, the DOS original game bundled with DOSBox) and instead you should use the community-made Source Port of the game called DXX-Rebirth. Give it a quick google search and you should be able to find it. It's trivial to get running (as long as you own the game yourself, which you obviously do) and you won't have any problems like this ever again.
2) I'm not sure, it's been a long time since I've run the DOS version of Descent. I'm assuming it's because you (iirc) don't/can't use the Enter button to change radio/check buttons like that. From what I remember, you can use the Spacebar to make your choice. Should be pretty easy to enable mouse and/or joystick and then configure those.
Escape button is kind of like modern controller inputs, it works as the B button for going backwards in menus. Spacebar rather than Enter is what they used for the A button analog, and you can also press the keyboard button like M, to go to the menu line item that starts with an M.
It's pretty neat to look at old DOS menu controls and see how much something as simple as navigating menus has changed and become kind of standardized.