It's the wrong way to string. You need a break angle otherwise the string curves over and has a higher action, until it finally sits after stretching over time. While it's doing that, everything is changing slightly. This is basic stuff.
Depends on the string and the design of the bridge, actually. I've been playing for, omg, a very very long time (decades), professionally, and never bothered with that. Partly because the "witness point" you speak of can change as the string stretches when it's new. So I intentionally avoid doing that and instead let the string form it's own "witness point" on the bridge saddle once it's been on there for a few hours.
But then I don't use particularly stiff strings, not flats, not very heavy, and I only use top mounted bridges so there isn't that stupidly heavy bend on the strings near the end.
I've had to use the "witness point" on a bass that had medium gauge strings and was being strung through body.... and it was just hell to get it lined up exactly right by putting force on it to bend it at the exact point that it wanted to bend.
So I'm not saying that witness points are wrong - they are, from my experience, very much related to the type of string and how it mounts on your instrument.
I also am extremely picky about very very low action and buzzing etc. It's not "doing it wrong" to not bend the string over the saddle. It's just situation-dependent.
I would ABSOLUTELY NEVER tell someone that they are doing it wrong if they don't bend the string over the saddles. It's not "basic stuff".