I think it should be noted that the idea of technology failing is one part "what is new" with one part "mana static." Most of the examples of failures are pretty high tech things (such as cell phones), or technology that is still "new" in comparison to humankind or to the wizard in general. The RPG mentions that the age of the wizard does often denote what sort of technology will act up around them. If a wizard from the 1600's were to use an older automobile, it probably would fall apart faster than the Blue Beetle at Dresden's hands.
With the way things are in the novels, we haven't seen anything less advanced than a television go on the fritz around Molly, and no problems with the Blue Beetle as far as we've seen. We also haven't seen semi-automatic weapons fall apart in the hands of the younger Wardens (remember, Carlos prefers grenades and semi-auto pistols when he goes into battle). We don't have much evidence by way of the older Council members, but we seldom see them with things that would have been "new" in their time.
The only time we've seen an exceptionally old Warden in a vehicle was in Turn Coat, when
Luccio (who is from the late 18th to early 19th century judging by the hints by Lara Raith) and Harry were lent a the Rolls Royce Wraith (production circa late 1930's if memory serves correctly) by Lara. Of course, she was in a new body and noted her powers weren't what they used to be,
so this could be the reason why it didn't fall apart.
Long story short: I don't think an older wizard would have learned to fly the planes from WWII due to them being "new" at the time, but I could see some of the new Wardens being able to take to the skies in such a way without causing too many problems, as they seem to be a bit easier on technology, as their perspectives of it and what's "new" is drastically different.
Again, this is all speculation, so take it with a grain of salt.