Sorry but that's an asinine reply. The people looking for the support are busy doing something and looking to pay a company for the support. If they had the time to volunteer for support, they wouldn't be looking for support themselves. You're the one touting Debian out of nowhere, you can't ask the people you're talking to, to volunteer to make your point better.
Debian handles all of these transitions by itself during upgrade process, and shows you a nice readme before starting all of them.
For example, Debian has finished two big transitions recently. Merging /usr and 64 bit time support. Both are done on testing, and even on testing nothing has broken.
Another big change (which also made HN front page via LWN) was /tmp behavior change. It's handled differently. If your system is already installed, it doesn't change the behavior, but new systems will behave differently.
All of these changes are again communicated via "NEWS" mechanism. If Debian changes a config file, it's replaced. If you modified this file, apt will ask what you prefer, and you can diff the file in place.
In the past, many similar changes are made, and all were transparent. If you're not using any external repositories which change tons of system packages with their own versions, nothing changes during upgrades for you.
While there's an extensive release note provided with every release like [0], the upgrades are pretty straightforward.
As a result, having a few or many Debian systems which are older than a decade is a norm, not an exception.
Then make it longer. The debian team is starved for volunteers and would love to have more long term maintainers.