For helmet, I just ordered my second Shoei J Cruise. The flip up face shield is most handy when it starts to rain, or, if I just want less wind/noise. It is also great when it gets cold. I have, on occasion, used the tinted sun shield, but am not a huge fan
For headsets, I have Sena, and currently use the 20S. Like anything new, there were some growing pains, but now I can communicate with my riding buddy with ease. My wife no longer rides, so I have no experience trying to talk with a passenger. I also do not have a CB, so I have no need for the Freewire. I do have an SM10, which lets me listen to my MP3 player and radio. If I had a passenger, we both could listen. I use my iPhone like I was not riding, and at 80 MPH I have had people amazed I was on my Wing. I have 2 units, and keep both charged. On very rare occasions I have had mine run down. On the next gas stop, I simply swap out the "brains" (part that has the battery/electronics) and put the dead one on charge in my trunk. If you are concerned about your battery life, when you stop for lunch, put your units on charge while you eat. (I have a dual USB charger wired in my trunk lid.) There will be plenty of battery to get you to your stop for the night, where everything gets charged overnight. Is learning to use the bluetooth as easy as a wired headset? No. Is it worth the effort to figure it out and learn it? For me, absolutely!