I'd be interested in hearing  other opinions about this. Out there in
> the "real world" (™), how long does Long Term Support have to be in
> order to be practically useful?

Two years to be able to stick with a single version? Just fine imho.

A few points you have probably heard before:

Django is just one layer of the stack. Extending support because other layers don't have a critical mass or a release cycle to provide new versions may not be a problem that Django should be expected to solve.

Growing the number of supported versions competes with evolving and keeping fresh. And evolution is critical for attracting and keeping contributing developers; LTS is not the interesting place to be in the long run.

Diverting (free) developer resources to keeping "large organizations" happy may be at odds with the benefits and tradeoffs of an open source project. If large organizations want to pony up developers or money then I'll bet they can keep an LTS release going indefinitely so there isn't really a conflict there. In my experience those organizations will provide those resources if they feel the added value is important to them.

If independent or contract developers are hoping to use Django to deliver software to other organizations then the support cycle needs to match the customers' needs. But that is between the developer and the customer to work out the best set of tools for the job.

If an organization won't consider a tool stack because it does not have an LTS plan matching their requirements, then I know of at least one organization which should not use that tool stack. They are making the tradeoffs, and can choose the best solution for their needs.

But in my experience, when someone locks onto a version for a substantial period of time, they will end up orphaning the product or they have (perhaps unwittingly) deferred the modest pain in keeping fresh on versions to feeling a large amount of pain later on when they upgrade. I prefer the pain to arrive in smaller doses.

Thanks for asking ;)

                          - Tom

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