1---No problem--I once rototilled my 400 ft, large (2 1/2") rock driveway (with a heavy duty tiller) and moved it 40 feet away.
2---If you rototill---- and then pack flat--- rocks will not surface to any degree. That has been my experience in maybe 600 acres. You must pack it flat, however.
I'm not exactly sure why but think my old days of science in school hold a clue. Maybe the flat surface creates some sort of "hydraulic pressure", for want of a better phrase, that causes the surface to remain level and the rocks to stay suspended. Much the way bananas stay below the surface of jello when it cools in the fridge despite it being stirred up when partially cooled.
Whatever rocks resurface over time you can simply pick up at your leisure a few at a time. And the ground will not be soft if you oack it firm with a heavy packer as I stated.
3--my vote is to use the tiller on a very slow speed as opposed to rock raking it. That way it stays level and rocks stay under. Raking the rocks will only leave a fair number that are partially exposed and ground that is packed hard. You'll never get them all by picking and I have tried every which way from Sunday to get rid of rocks.
So, evaluate and follow your path.
EDIT--it would help if you filled in your info a little bit so we could guess at your soil type, glacial till, etc.