@polotek My gut says that most *people* don't, because the VC bubble has taught us that apps are free. Software engineers just aren't that different.
It doesn't help that many of us are building free apps for consumers, internal tools, or B2B stuff. Those environments don't necessarily teach the intuition that, yeah actually, it makes sense to pay $50/yr for YNAB or $200 for OmniFocus or whatever. Because what we learn from our jobs is "apps are free" and "paid software is for businesses".