Where do you hope we would start the game?
Consider the strategic positions, the faction divide between Imperial forces and rebels, the scenery variety, and interesting vista, and so on...
Personally I think that near Riften would have a really nice and welcoming scenery to start a game, but near Falkreath would have a more strategic place, between both sides of the war.
Starting in the middle, near Whiterun, would have more access to all the sides of the map, but would make the game seem a little bit smaller, and it is usually more recommended to game designers, to start from a side of the map, and let players continue to the other sides.
Sorry, for the second question, there was no room for "NONE" choice, so threat it as "if you had to choose!" if your first choice was, "Near no settling.".
Please tell us why chose what you chose.
My choice is near Riften.
Edit: But personally, I would select any settling primarily within the Rift hold, and secondarily within Falkreath hold.