I have a 2014 Berkshire with the 340 and same transmission. I have had the exact same issue in the year since we purchased. I came across a thread somewhere and for the life of me cannot recall where I found it. However, it stated that the turbo boost will not react well if the engine has idled at low rpm's for any time. They suggested to high idle at 1200 rpm if idling more than 5 minutes. Since following this process it has had a noticeable effect although we have still had occasions of needing to manually downshift on the hills. There are three idle modes. Normal, medium(950 rpm) and high(1200 rpm). On my unit, high is achieved by pressing the cruise control set speed button. Medium idle is set by pressing the resume button.
I have not been able to find further documentation on this and it may have been on a trucker forum. So far is has been working. I know there are many discussion on pros and cons of high idle but for me this has been working. If anyone has more on this or the high idle and turbo boost please let us know.