Wind the clock forward and it becomes not just central to life but understood as well, the same reason why the Blue Beetle works better than more modern cars or a revolver more than a modern gun, for wizards after Harry's generation a modern gun and a modern car are normal.
I don't understand what you mean by this. The wizards' judgment isn't what makes it work and the reason it has less effect on older stuff is because it's generally less complicated.
Techbane is like paradox in the sense that its rules don't care about what the mages think about what is going on. Moreover, the time scale we're given on how it changes allows for wizards who are living in Harry's lifetime to have experienced the change over but no one is standing around under the old rules free of the stuff.
When the rules change they change for everyone. Some people getting to break them outright makes as much sense and iron only being conducive for some people.
The major reason I can think of for this discrepancy is the fact that Daedalus just doesn't have full Wizards or major talents so they can just completely circumvent Tech Bane. Dresden is a particularly powerful wizard and he can still drive a car with a combustion engine it doesn't matter that it's 20 years old by the time we get to see it first time it's still a modern vehicle. Never mind using the guns that he does that are visually old-timey but newer than his car both in design and material.
If techbane is as crippling or as obvious as you were saying then Wizards literally would be relegated to Towers but we know that they go to college they can be near electric lights and cityscapes.
Edit

Dragon ninja
Techbane is actually that hard to live with and most wizards don't live in major cities. It's a plot point that it's too dangerous for the average wizard to fly on commercial airlines, and Dresden lives in an apartment so unfinished it's probably illegal to rent out. His car is substantially older than that and still breaks routinely.
Anyone with enough magic to do more than give themselves a headache destroys any electronics they regularly interact with. It's how it works.
A minor practitioner can get away with living a more modern life, but they do it by not rubbing their magic all over modern technology.
2006-2007 is at the point, where technology is also starting to become an alienating influence by itself, though. A programmer or a research and development engineer in electronics and such exist in a wholly different world than normal people, and operate using different terms. They are hard to understand by normal people, and may struggle to understand them in turn. Hell, look at
this. And this is not a joke. There's something to it, where older generations are alienated by modern IT infrastructure.
So? It didn't change for the course of the Dresden Files under those same conditions. Magic isn't measuring a threshold of sufficient isolation then stopping, it's imposing a rule that isolates you more than other people in a comparable circumstance would be.
More generally, is this the Dresden Files or not? How many iconic features and plot beats can be cut away it's a generic urban fantasy setting with some character imports?
Sure we brought a demon planet of the stuff with us, but it's a different paradigm that's by design at odds with the world that the plot has to grapple with reconciling. The huge deviation is the point. This is just going "nah, they totally can do that when it's convenient, world building be damned".
It's especially annoying that the dumbest motherfuckers on the planet are building stuff that shouldn't be possible and getting away with poking things that should killed everyone involved in the thought process of designing it like the saw.
The whole thing validates the attitudes Daedalus has to the supernatural.