I can only comment on the career progression but I would say that like a lot of pilots considering a career in rotary wing you've got the cart before the horse. I personally don't think it is worth worrying about where your career will ultimately end up. What may seem appealing as a future job now may seem much less so as you gain industry experience and knowledge. No doubt there will be highs and lows along the way and once working opportunities are bound to come your way that you haven't considered yet.
My suggestion is, if you really want to fly for a living, just take it one step at a time. Get your medical, get a license, get a job, get some hours and experience and then make the most of the opportunities when they come along.