On the other side.
Good questions. The answers I like and so will you. Like I said in my previous post I haven't been dealing for that long. From the experience I've gotten most dealers don't know jack about counting cards. Furthermore, none of the pit has bothered to teach us. They just want us to follow procedures. By the book.
As for placing the cut card that is written in a manual but doesn't specify why to my surprise. We do have to follow these rules or there are moderate consequences.
However, on a 2 deck game we are to place the cut card at one deck(50%). If caught not doing so it will result in suspension. But even with those rules my fellow dealers still put the damn cut card at 65% to even 75%. I do it sometimes hoping the shoe will stay good, thus giving me more tipping opportunities. But to answer your question I don't think dealers know why they put the cut card where they do. Some do but not most.
As for the average pit boss being able to catch a counter. I may not be the most experienced guy to answer that but there are a few floormen who are knowledgable and in my opinion can catch one. However, I think the average pit boss can't unless you give yourself away by not using any cover or by winning an excessive amount and then having your play evaluated. Hiding chips and not playing to excessively in one place I think are some of the best plays you can do.
A few of my friends who also deal but at other Casino's know that I'm an AP and have agreed to give me more penetration however mostly on 6 deck.
But there are dealers who will bend the rules especially if you tip them. Nothing big even just a nickel bet every now and then. Or even a dollar bet on five straight hands. Whatever you can afford.