Good Morning Andrew,
First, please look at the resources to make sure they are in the proper Ad package. You can do this two ways.
1) From Local Ads- click on the package that you believe your ads are running in and see if they appear in the content area. Then look to the right sidebar and make sure the dates are in deed correct while you have "Play only between dates" selected.
2) Click on the resource in the timeline and see the ad package it belongs to under the properties area within proof of play. Again, making sure that "Proof of Play' is checked. Now select Save/Upload from the menu.
You also want to make sure that the proper campaign is assigned to your player. I only suggest this as some may duplicate campaigns to "test" out the ad network and do not realize that they forgot to switch the campaigns in the player. So the original is what they are seeing and of course will see content playing that was scheduled for the future and proof of play is not set in that campaign.
As for updating, I believe you will need to update all of your players manually that were not updated to the latest release because they were either beta or pre-beta and to prevent those from updating to a beta and causing issues, the auto-update was turned off. Once you have updated all players to the latest (Stable) release, your players should be able to update via the update button.
I hope this helps.