Welcome to the community! Some answers to your questions are below. Feel free to PM me for more detail.
pemery wrote:-I still have 16 months on my current order...should I expect to finish up my time here in Boston or transfer to the next available IWOBC class? -What is the normal (if there is such a thing) timeline for the redesignation to be complete?
You really need to ask the detailer as much will depend on minimum tour lengths, class up dates, etc.
pemery wrote:-I know an IWO first assignment is usually at one of the four NIOCs but does placement at one of these locations dictate the follow on operational tour. For instance, I am very interested in the NSW and CommEval positions, is there a NIOC that feeds into one of these?.
Short answer, no. However, there are Comeval billets in both Georgia and Texas so if that route interests you, and you don't mind doing two back to back tours in the same location, that may work out. Or you could at least get exposed to what they do by being co-located. For NSW, there is no set career path to get you in the door. But operational experience from one of the big four, and a possible TAD assignment supporting SOF, will help build your resume.
pemery wrote:-As a former P-3 guy I am very interested in EP-3s but with the P-8 transition is this still a viable path? I hear the mission is going to be picked up by BAMS in the not so distant future.
Ahhhh, the mighty EP-3. They were supposed to be gone a long time ago yet they continue to fly. I don't think we have a clear path ahead. My bet is they'll be in the air for a while. Maybe one day they'll be replaced by a UAV but I don't see that happening soon. Given your timeline you could easily get some EP-3 experience while the transition is planned.
Hope this helps. Again, PM me if you have more specific questions.