To reiterate; the paddlefloat reentry is a last ditch option, not the first.
While I've practiced the paddlefloat reentry in rough water with big chop, it's dicey, but should be able to be executed in less than a minute once the paddlefloat is inflated and fixed to the blade. You can do it in sizeable chop but it does have it's limitations and I recommend practicing this in the biggest conditions that you expect to paddle in...with assistance available in the form of another paddler who is practiced in assisted rescues.
As far as the order of reentries when solo - in my mind, at least; roll, reenter and roll, cowboy or paddlefloat reenter and roll, paddlfloat without stirrup, paddlefloat with a stirrup. The stirrup will lash the paddle around the boat and provide a stirrup to get you up onto the boat but will also require some practice before you really need it.
The key, as with anything, is good practice. Also, practice doing it without using rigging to fix the blade to the boat.