I think this is an important point you raise, which potentially also influences how many accounts go inactive each month.
I don't know who your target audience is. Probably not me. I'm severely underusing my instance due to continuously shifting priorities and lack of time. But when I'm working on it, it's in bursts. If a burst (of time) gets frustrated because I need something relatively simple done that I have no access to, it's dropped for that time and priority for the project goes down a few spots. Raising a ticket on a forum for something technical nobody but an admin can help with, can be a threshold for some people.
Considering what I paid for it I'm definitely not complaining, but a new server does not fix any of that.
As for the list of items you potentially 'should', we can't see which of those are going to be the most work. If any of those can be implemented without too much work for yourself and the rest of the team, it would be a quick win. If a couple of quick wins can significantly shorten the list, that would be a big win.