As someone who found a bit of an interest in fountain pens some years ago, I understand and shared your penchant to go for super-premium when it comes to timeless items. I have bought the occasional $500 pen (Graf von Faber Castell and Caran d'Ache have a couple of very beautiful items), but after one of the more expensive pens suffered some scuffs from light use and a friend of mine broke another one's clip, I came to the conclusion that I have a tendency to, as they say, break shit. I enjoy using them. To me, the little marks in the pens' platinum-covered cap don't take away from their sentimental value, but if I were to ever try and sell them, I wouldn't hope to ever get my purchase price back. The same, I believe, holds true for watches. When I noticed I had lost my $30 Cadence in a Metro, I barely scoffed. Since I had liked the design, I had an identical backup at home. Losing a timeless super-premium $10k Omega, on the other hand would've been a more severe problem. The pens, the Rolex watch and many things like them will retain their value just fine -- if you never touch, use, or in any way enjoy them.
My initial comment went in exactly the same direction as yours on midrange "luxury" items, with the possible difference that I would consider an iPhone, the beats earphones or (to a lesser degree) the Tesla as the midrange pseudo-luxury choice. In my opinion, a large part of the retail price of each of those lies in the brand value and in the marketing done by those brands. As I view it, their prices are determined not by their cost or performance, but mostly on what the customers will pay. In my perception, the midrange choice (Shure Earphones, Nexus or -- as others mentioned -- Moto E/G, Jetta) more closely reflects the cost to manufacture the item. Their profit margins are slimmer and, more importantly, more consistent.
As a final point, my apologies to Kia. Being European I tend to stick to public transport, rarely drive, and if so, tend to get cars with a manual gearbox. I was going to go with Dacia (Renault's Low-End Brand, I believe) first, but couldn't tell how well-known they were in the States. I also was under the impression that VW's interior was considered to be of rather high quality while I have read some negative comments on Tesla's.