I've seen quite a few posts on different forums over the last 2-3 years that contain the following:
-newbie
-installs Debian Oldstable rather than Stable
-on a desktop machine
-usually has more recent piece of hardware foo which doesn't run or run well on Oldstable.
Now, when it happened back when Jessie came out, it wasn't really odd, given that some newcomers might have had some former Linux knowledge and then decided to stick to a systemd-free system. But what is the upside of having Jessie over Stretch? I can't say that Stretch is significantly less stable or that Jessie got more stable over its course as a Stable release. What do you think?