RE: High end first?
I would say that if you are looking to do this as a commercial venture, you are going to be flying around people, parked cars, buildings and such. (unless you plan on taking pictures of open fields)
Yes, you do need the higher end model heli piloting skills. Take off and land is not enough. Once you are in the air, you will have to be able to safely control it no matter what happens.
Get a sim.
Get any smaller electric heli. It does not need to be a 3D monster. I would recommend something along the lines of the T-Rex. Learn to fly it. Learn to work on it. (yes, repair and troubleshooting are skills you need to develop). THEN consider getting the big bird.