I usually try to indicate our favoured releases, but my verbose announcements have been rare of late while we release the bleeding edge TS stuff.
We generally have two releases going: a stable release branch and a new feature branch. The stable release branch is currently 1.11. We will continue to do bugfix and minor updates only to that branch for some time. The most recent release on the stable branch is always considered the "most stable" for that major release's set of features. Right now that is 1.11.5.
Whether you always need to be running the very latest stable release though really depends on the account. Some bugs, such as the upload problem you encountered, are obviously going to effect any 1.11.1 installed account. For bugs like that, effected accounts should be upgraded right when the fix is announced, to minimize the install base and future grief.
Most of the time however bugs are much more localized in terms of both the releases and accounts effected. We try to give a "bug window" for a given problem to indicate in which release the bug was introduced. At the end of the day, support people need to review the readme and determine whether a problem is going to effect an account given their current release and feature requirements.