If I told you I've never had crimped connections fail, you should seriously question my expertise! I've done lots of crimped connections the way you show, because in a pinch when you don't have the right tool, it is certainly the best alternative.
The idea that an insulated terminal can be crimped until there is no air between the strands is bunk. No plastic exists that can take the pressure that requires. So an insulated connector is NOT going to be as mechanically good as a noninsulated connector. So putting heat shrink over a properly crimped bare connector would be the best of both worlds, but it takes longer. However electrical efficiency and mechanical strength are not the same thing. So how much mechanical strength do you really need?
I think the big issue with insulated connectors and crimpers is whether the tool was designed for the connectors, and is of good quality. I'd bet if you checked with Ancor they test their tools on their connectors and no others. Their engineering says that works, and they guarantee. Use someone else's tool or connectors and you have introduced a variation that no one can control.
I have been building electrical panels a long time time used crimped connections. The first was a control panel for unloading dry powders from rail cars 45 years ago, when I was 11. I'd been working with my dad, an electrician, during the summer when he got the job to build this panel. We drew up the electrical schematic together, and I actually wired it in the shop we had in our garage.
So over the years I've owned just about every crimper you have ever seen. I have a couple of very good ones though, that don't work worth a damn. My suspicion is that they are worn out, but don't look it, need some kind of adjustment, or only work well with specific connectors.