Go straight to the top and get a Mavic Pro. It has a beginners mode, tripod and cinema mode that restrict speed heights etc so that you do not get into serious trouble. From reading this site for 4 months I see that most problems of failure are caused by pilot error ie. flying when too windy and by not being in line of sight.
Mavic Pro has been out for a while, and while it can fly longer and farther, from what I have gathered so far, the quality of footage is lower than that of the Mavic Air. And since footage quality is crucial for what I do, the Air is what I'd go with. Also, my intention is to upgrade to Phanton 5 once it's out (and I know how to fly it), so my hope is that I'll lose less once I sell the Air.
I think I'll get a cheap drone just to get a sense of how things work, then I'll go with the real thing. Thanks to all for your answers, this has been really useful.