You can always experiment (and get answers to these questions) by signing up for a free Apps account.
Since you know what you’re doing, I recommend that you set up an Advanced WordPress account and retain the admin account for yourself. Give your users their own logins that are set their role to Editor. They’ll be able to do anything except change the features of your site. In other words, content only.
A one-click Advanced can be set to auto-update, which is similar to the Easy install. Except as an Advanced install, you won’t face any limitations you’ll regret later.