The process of apps installed via addons seems to be a bit flakey/inconsistent. I've seen everything from apps being available immediately to users having to log out and back in to see them. There is also a known bug for jive hosted/on-prem where federated users do not get add on apps installed.
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One option to provide some of the experience you are wanting. You can bind an app to do only be available for a specific security group. (Not sure when it comes to canvas view, but you might even be able to filter on ExtProps of the user, but I'd need to check on that). Either way, with either of these restrictions in place, you simply lace the action you want to monitor with a trigger to either Add ExtProps or membership to the securityGroup and the App should appear as desired.
Hope some of that helps, but again ... NIls' feedback is being looked at internally on how to improve the user experience.