All of my Macs are on 14.4.1. Additional note to problem 1 - as soon as I logged in after restart, I opened the Cookie app. It said that I needed to Purchase Cookie in the upper right corner and I was unable to turn on automatic removals . After waiting a few more seconds for it to load, I saw that the purchase status cleared and I was able to turn on automatic removals
It's as if it is starting up before my Mac gets internet, and since it doesn't think there is an active subscription it turns itself off?