I would for sure rather dump in a free coin counter than re-roll.. But there are a few variables, that you will learn and expirience in time. For instance, I very rarely can walk into a bank with a coin machine and dump $1,000 dollars in halves without jamming the machine, filling it up, breaking it... etc. (which when any of those things happen, I will usually end up spending more time sitting there at the coin counter than if I just re-roll the halves and do it that way). It is also going to depend on where you are wanting to dump. If you order from brinks, and then dump back at a brinks bank, you will going throuh your own dumps in a very short amount of time. (in my area anyways.)
As far as honesty, I hear what you are saying, the big deal about talking to tellers is that once you or I educate them on silver coin, and then they figure out how much they are worth and how easy they would be to find being a teller... You have just added one more person to compete in a game that is becoming harder and harder to score in because of all the new competition. What is even worse about a teller who is now a silver hunter, you just had a pick up bank go from where your chances of getting silver are going to go down significantly because any silvers will have to sneak past the teller(s) now, where as before, if there was silver, all you had to do was pick it up... Make sense?
I also agree though about the "honesty" policy, you just have to be selectively honest. For instance, when a teller asks me about why im interested in so many coin etc... I will usually play the "I'm a collector" card. If (and it happens very rarely where I am) the teller says, oh, you looking for silvers.... The answer is simple, "well silver is always nice but it has gotten so rare to find anymore that I do not anticipate finding any. then I usually switch it up, by asking them a question... Why do you mention silver? Did you find any? Do you have some?
Anyways, good luck to you...