Hi Ian,
Thank you very much for your timely and detailed reply - most useful.
To be honest, the deployment wasn't overly difficult in comparison to some of the products our users ask for. If I was being nitpicky, I'd say that an MSI would be more useful for enterprise deployment, but it isn't a anything we can't script.
In terms of the environments etc that you speak of, I am not familiar with the software at all to really comment too much. I'm not 100% sure the user is totally sure what their issue is precisely, so I guess figuring out what their issue is would be a good start. We keep quite a tight control of what our users can and can't do on our machines and so multiple environments for different users may complicate matters somewhat.
It sounds like the users managing their own updates would be easiest if they are as frequent as you say - we don't have the time to work on packages too many times a year as it is.
Thanks again
Andrew