1. upgrades do not survive reboot. Constantly redownloading takes precious time and could lead to a form of identification due to increased frequency/patter/psuedo-fingerprint.
2. The additional software will ONLY install IF there is an internet connection. If you have a vital app, to say this is problematic is a serious understatement.
In addition, a GUI button to retry the installation would be very nice. Let's not forget the main users of TAILS aren't computer savvy. They are reporters, and all the other careers and people you have listed.
3. The Control Port is always open on every reboot. How about a password hash on the login page, just like with the encrypted persistent drive? It would be best if they are different. At present, I have to:
1. Stop tor service
2. open another terminal to hash the password.
3. edit /etc/tor/torrc file, save, exit.
4. restart tor service.
That's a lot of time and steps for a non-techie user.
4. Sometimes tor stops with no way of knowing. Can we have the onion turn red when this happens? It is supposed to have an x on the onion, but sometimes tor is down and there is no indication until you try to open a new tab on the browser, or, if closed, initially open the browser. Messages say Proxy issue, with browser already open. And tor not ready, if you are initially, or subsequently reopening it.
That's all the significant things I can find at the moment.