These are completely unnecessary problems caused by Garmin sometimes not thinking through the most obvious scenarios. The whole database update process is unnecessarily complicated and insufficiently documented - leading to lots of different opinions and ways of doing things that should be simple and straight forward. It's complicated enough for the aircraft owner, and a big recurring headache for flight schools.
The NAV DB fortunately waits until its active day to ask if you want to install it, but flight charts installed a day earlier than valid day leads to "outdated charts". Garmin's DB Manager software is definitely better now than it used to be, but they still leave too many details unclear, and the details are - as we all know - where the devil lives (i.e. DB issues rendering the whole system unusable for IFR - or even all flight scenarios - until resolved).