I'm curious as to how someone mentioned using a power rake. Not that that would be a bad way to go, but kind of like wearing a tux jacket with jeans and tennis shoes to a ball game. Just doesn't seem to fit in with the rest of the plan.
My two cents worth:
A. If you have never used a tiller before, I would not recommend trying to learn on this site condition. Think of learning to drive on a freeway or downtown. Yes rocks can damage the tines, but you would almost have to be cramming it in the soil to do so. If I try to make a mini dig like my 8HP, yes. If I try to make my 8HP dig like a tractor, yes.
B. If I were going to hire someone to use a power rake, I would try for a good price on a little more work and have them do the prep with bigger equipment. A power rake is the finishing touch, after all the hard work is done. Not to suggest that trying to go backwards, straight, in the dust, with a 10 mph wind, is not work. Personally, I would use a rock rake or a gill-rake pulverizer.
C. What area yard do you plan on for lawn that you need rocks removed from? Could you (or hire someone) rake them out the old fashioned way?
D. Would you be comfortable operating a small tractor? HD rents them also.
E. I would use, or hire, a tractor to break up the area first. Better suggestion if I knew what size area. One option would be to run over it with an all purpose plow to break up the top six to eight inches, then go over it with a tiller. Also, the AP plow will get a lot of those roots and rocks out. A lot of times, that's a PITA, but in your case would kill two birds with one shot. Or, get a PTO tiller but you won't get nearly the depth and this would not be my first choice because of that. And/or, if you are planning on planting very many shrubs and trees, a backhoe is really useful. I'm kind of spoiled with mine at work, so I don't do as much at home with a shovel anymore.

Bottom line, use some equipment to do the heavy work and get that out of the way, then just buy a tiller and learn to use it in soil that is already loose. Like learning to drive on back streets. I presume you are buying and looking to do this for the long term. You would be surprised what I have seen renters do though!