You can leave the Move on the charging dock to keep it fully charged so it will always be ready to be taken on-the-go when you need it. Leaving it on the charging dock will not reduce the battery’s lifespan.

I purchased the Move Because of the battery and the ability to use my music collection on my NAS. There were 2 issues first it took 2 calls into support to link to NAS as the first person did not know anything about the NAS but thought he did . My Second call resolved most issues however there is a limit to the Size of your personal music and the Software is poor at best but does work.  its advertised as being able to provide music for 10 hours. I went on vacation put it in my suitcase turned off landed 15 hours later and did not even get 5 hours at low volume this was a mistake, I attempted to use a usb-C charger and that did nothing also . Not sure what is going on I hope it gets better with updates in software.  

As a guess, for part one, you put the Move in standby, rather than turning it off while it was in your luggage. For part two, it would be useful to know the power ratings (amps and volts) on your charger, as I suspect it isn’t strong enough.

Do you really mean a Roam, not a Move?