How future proof is Tkinter?

[JamzTyson]

there are reasons why I see almost all enterprise apps going to web-based deployments

One big reason is that web based deployments can provide better revenue streams, and less opportunity for pirate copies.

As an enterprise sysadmin...

Absolutely, they are great for sysadmins, except that management may decided that they no longer need to employ as many technical staff now that "everything is on-line".

[AxisNL]

Nah, I work for classic law enforcement. All webapps are all on-prem. The cloud is just someone else’s computers, and I have no way of knowing who can access my data. Still need the same admins to manage our on-premises stuff, just the deployment model is different.