The stiffness of new leather soles can cause rapid wear on the tip of the sole . Wearing them on a non-abrasive surface until flexible can prevent or reduce this .That is what the carpet thing is about.
The pencil crease is really a matter of preference I personally prefer the look of natural random creasing but I dont feel there is anything "wrong " with it .
I dont think you are overthinking this at all. New shell cordovan shoes are an expensive investment and these are pretty basic questions .
Do I have to break in a flex welt LHS suede on the carpet for three days? Will that ease toe wear on sole? I usually install plastic tap...
Edited by Profligate47 - 5/29/13 at 6:09pm