I'd call Monaco... 877.466.6226 as it's a RR10S Roadmaster BUT a intermittent problem is a pain to solve. Assuming the front comes up and both air gauges are 110+ psi it's not the air dryer or a air leak. It's not the tag axle as it by it's self cannot raise the back. There are two ride height valves on the rear drive axle which controls the height of the rear axle, but it's the HWH air leveling that is the only thing that would control/stop both of them from working properly assuming you have 110+ air pressure.
When this happens I'd try raising the back by pressing the Level button twice on the HWH control panel and then the up rear arrow. Once up, put the Allison in D, see if it stays up. If it does not stay up then I'd raise it again, but hit the Emergency Stop button (lower left) before putting the Allison in D... you do not have to actually move. I agree it's a HWH air leveing problem. If it was the front with only one ride height valve then it could be either.