Hi J-Rod and welcome to PPrune.
You might want to check the rotorheads part of the forum to meet all the... well, rotorheads! Its a part of the site dedicated to whirlybirds.
I dont know the situation in the US, but in the UK there are a few flying colleges that provide integrated or modular courses to get you into a career as a chopper pilot.
I had my assessment for a college called Cabair in England with a chap who was going for the helicopter route, and he was asking the same sort of questions as you just did. If I remember rightly, the answers he was getting were along the lines of:
You will need experience before you can consider Police/Air-med/Fire etc - Basically the very specialised jobs. He would likely gain the experience required flying out to the Oil rigs in the North Sea.
As i have said, I dont really know much about the scene in the US, but perhaps the equivelent jobs would be pleasure flights.
I got the impression that to get to the exciting stuff, you have to endure the mundane to get those all important hours.
Anyway, Good luck and I wish you all the best!
JB