There are not many cross-trained guys out there. Most rotorcraft guys stay with the helicopter industry, and the fixed wing guys stay with fixed wing. There are some out there, but most stay with one or the other. In the fixed wing field the vast majority of A&P's will tell you they know nothing about a helicopter.
I know guys that can do a landing gear overhaul or an engine change on a fixed wing aircraft practically with their eyes closed. But if they had to change a rotor head or a transmission in a helicopter they would be lost.
The exception is avionics, those guys work on both fixed wing and rotorcraft; the avionics are the same.
Sounds like you have a good plan. The only other thing I would recommend to you is to study FAR 43 and 65. I've had ex-military guys work for me and they knew the military way of doing business but not the FAA way. And for some people it's hard to get them to conform to the FAA requirements after years of being in the military. In my current job I deal with FAR 21, 23, 25, 43, 45, 65, 91, 135, and 145. If you know the regs as good as your FAA inspector does, life is easier in this regulated industry.